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Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Jiupeng Liu, Shuo Tang, Shichong Wang, Mengting Cao, Jingjing Zhao, Puyu Zhang, Pan Li
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Chiral Counteranion-Directed Catalytic Asymmetric Methylene Migration Reaction of Ene-Aldimines J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 Norie Momiyama, Chanantida Jongwohan, Naoya Ohtsuka, Pawittra Chaibuth, Takeshi Fujinami, Kiyohiro Adachi, Toshiyasu Suzuki
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SN2 versus SN2′ Competition J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Thomas Hansen, Pascal Vermeeren, Lea de Jong, F. Matthias Bickelhaupt, Trevor A. Hamlin
We have quantum chemically explored the competition between the SN2 and SN2′ pathways for X– + H2C═CHCH2Y (X, Y = F, Cl, Br, I) using a combined relativistic density functional theory and coupled-cluster theory approach. Bimolecular nucleophilic substitution reactions at allylic systems, i.e., Cγ═Cβ–Cα–Y, bearing a leaving-group at the α-position, proceed either via a direct attack at the α-carbon
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Porphyrindiene-Based Tandem Diels–Alder Reaction for Preparing Low-Symmetry π-Extended Porphyrins with Push–Pull Skeletons J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Guanyue Cao, Glib Baryshnikov, Chen Chen, Liyuan Chen, Tengjiao Zhao, Shuyi Fu, Zhenhui Jiang, Xiujun Liu, Qizhao Li, Yongshu Xie, Chengjie Li
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TEMPO-Promoted Mono- and Bisimidation of Tertiary Anilines: Synthesis of Symmetric and Unsymmetric N-Mannich Bases J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Xiu Juan Xu, Adila Amuti, Wen Jing Hu, Qiaerbati Adelibieke, Abudureheman Wusiman
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Heptagon-Embedded π-Expanded Thieno- and N-Methylpyrrolo-Pyridazines with Substantial Out-of-Plane Dipole Moment J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Masato Hisada, Daiki Shimizu, Kenji Matsuda
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One-Pot Synthesis of α-Amino Bisphosphonates from Nitriles via Tf2O/HC(OR)3-Mediated Interrupted Ritter-Type Reaction J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Ya-Cheng Hong, Jian-Liang Ye, Pei-Qiang Huang
A versatile synthesis of α-amino bisphosphonates has been achieved through one-pot interrupted Ritter-type reaction under mild conditions. The reactive Ritter intermediate nitrilium is in situ generated by treatment of nitrile with readily accessible Tf2O/HC(OR1)3, which is trapped by phosphite ester to deliver the desired product. This protocol is efficient, scalable, and well compatible with a broad
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Enantioselective Friedel–Crafts Reaction of 2-Alkynyphenols with Aromatic Ethers by Chiral Brønsted Acid Catalysis J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Wenxuan Zhang, Jiaying Sun, Zhendong Lian, Ran Song, Daoshan Yang, Jian Lv
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Stabilization of Glucosyl Dioxolenium Ions by “Dual Participation” of the 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Protection Group for 1,2-cis-Glucosylation J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Wouter A. Remmerswaal, Kas J. Houthuijs, Roel van de Ven, Hidde Elferink, Thomas Hansen, Giel Berden, Herman S. Overkleeft, Gijsbert A. van der Marel, Floris P. J. T. Rutjes, Dmitri V. Filippov, Thomas J. Boltje, Jonathan Martens, Jos Oomens, Jeroen D. C. Codée
The stereoselective introduction of glycosidic bonds is of paramount importance to oligosaccharide synthesis. Among the various chemical strategies to steer stereoselectivity, participation by either neighboring or distal acyl groups is used particularly often. Recently, the use of the 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) protection group was shown to offer enhanced stereoselective steering
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Enantioselective Conjugate Addition of Boronic Acids to α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Chiral Diols J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Guo-Li Chai, Ping Zhang, En-Ze Yao, Junbiao Chang
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Phospha-Michael Addition on α-Fluorinated Acrylates: A Straightforward Access to Polyfunctionalized Fine Chemicals J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Xin Huang, Tatiana Besset, Philippe Jubault, Samuel Couve-Bonnaire
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Straightforward Synthesis of Alkyl Fluorides via Visible-Light-Induced Hydromono- and Difluoroalkylations of Alkenes with α-Fluoro Carboxylic Acids J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Chunfang Guo, Xuliang Han, Yu Feng, Zhaolong Liu, Yueyun Li, Hui Liu, Lizhi Zhang, Yunhui Dong, Xinjin Li
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Regioisomerism in Symmetric Dimethyl Dialdehydes Dictates their Photochemical Reactivity J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Florian Feist, Leona L. Rodrigues, Sarah L. Walden, Christopher Barner-Kowollik
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Functionalized Cyclopentenes via the Formal [4+1] Cycloaddition of Photogenerated Siloxycarbenes from Acyl Silanes J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 João R. Vale, Rafael F. Gomes, Carlos A. M. Afonso, Nuno R. Candeias
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A Visible Light Ru-Catalyzed Photoredox Access to Substituted Dihydrofurans J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 Jorge Victoria-Miguel, William H. García-Santos, Alejandro Cordero-Vargas
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Deracemization of Binaphthyl by Suzuki Diarylation: The Role of Electronic and Steric Effects J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 Filip Bulko, Michal Májek, Martin Putala
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Flexible Approach for the Synthesis of Annulated 4H-Pyrans Based on a Cu(I)-Catalyzed C-Allylation/O-Vinylation Reaction of Cyclic 1-Bromoallyl Tosylates with Cyclic and Acyclic 1,3-Dicarbonyls J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Mehran Khoshbakhsh Foumani, Jürgen Conrad, Wolfgang Frey, Uwe Beifuss
The Cu(I)-catalyzed reaction between five-, six-, seven-, and eight-membered cyclic 1-bromoallyl tosylates and five- and six-membered cyclic 1,3-dicarbonyls in DMF at 80 °C using Cs2CO3 as a base and 2-picolinic acid as an additive selectively delivers a wide array of bisannulated 4H-pyrans in a single step with yields up to 92%. The transformations are considered to proceed as intermolecular C-al
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Cobalt-Catalyzed Formation of Grignard Reagents via C–O or C–S Bond Activation J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Ewa Pietrasiak, Seongmin Ha, Seungwon Jeon, Jongheon Jeong, Jiyeon Lee, Jongcheol Seo, Eunsung Lee
C(aryl)–OMe bond functionalization catalyzed by cobalt(II) chloride in combination with a nacnac-type ligand and magnesium as a reductant is reported. Borylation and benzoylation of aryl methoxides are demonstrated, and C(aryl)–SMe bond borylation can be achieved under similar conditions. This is the first example of achieving these transformations using cobalt catalysis. Mechanistic studies suggest
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Arylselenyl Radical-Mediated Cyclization of N-(2-Alkynyl)anilines: Access to 3-Selenylquinolines J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Changlei Zhu, Max Nurko, Cynthia S. Day, John C. Lukesh, III
An efficient and novel approach to accessing 3-selenylquinolines from diaryl diselenides and acyclic, selenium-free substrates is described. Preliminary mechanistic studies indicate that the combination of CuCl2 and air affords an appropriate environment for producing arylselenyl radicals that initiate the cascade cyclization of N-(2-alkynyl)anilines, forming key Se–C and C–C bonds in a single step
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Nickel-Catalyzed Tandem Ueno–Stork Cyclization: Stereoselective 1,2-Dicarbofunctionalization of Cyclic Alkenes J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Pedro de Andrade Horn, Hunter S. Sims, Mingji Dai
A nickel-catalyzed tandem Ueno–Stork cyclization is developed to enable stereoselective 1,2-dicarbofunctionalization of cyclic alkenes and efficiently build various bicyclic products. This new protocol does not involve any toxic or difficult-to-remove tin reagent and is scalable and amenable to build all-carbon quaternary centers.
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Selective C3-Allylation and Formal [3 + 2]-Annulation of Spiro-Aziridine Oxindoles: Synthesis of 5′-Substituted Spiro[pyrrolidine-3,3′-oxindoles] and Coerulescine J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 SK Abu Saleh, Atanu Hazra, Maya Shankar Singh, Saumen Hajra
Brønsted acid- and/or Lewis acid-catalyzed selective C3-allylation and formal [3 + 2]-annulation of spiro-aziridine oxindoles with allylsilanes have been demonstrated to deliver direct access to 3-allyl-3-aminomethyl oxindoles and 5-silyl methyl spiro[pyrrolidine-3,3′-oxindoles], respectively. The acid-catalyzed methods do not provide any stereoselectivity when chiral spiroaziridines are used. However
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One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Ilya P. Filippov, Mikhail S. Novikov, Alexander F. Khlebnikov, Nikolai V. Rostovskii
A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared
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Synthesis of β2,2-Amino Acids by Stereoselective Alkylation of Isoserine Derivatives Followed by Nucleophilic Ring Opening of Quaternary Sulfamidates J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Pablo Tovillas, Claudio D. Navo, Paula Oroz, Alberto Avenoza, Francisco Corzana, María M. Zurbano, Gonzalo Jiménez-Osés, Jesús H. Busto, Jesús M. Peregrina
Chiral bicyclic N,O-acetal isoserine derivatives have been synthesized by an acid-catalyzed tandem N,O-acetalization/intramolecular transcarbamoylation reaction between conveniently protected l-isoserine and 2,2,3,3-tetramethoxybutane. The delicate balance of the steric interactions between the different functional groups on each possible diastereoisomer controls their thermodynamic stability and hence
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Synthesis of Nitrogen-Doped Aza-Helicenes with Chiral Optical Properties J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Xue Gong, Chunmei Li, Zhixiong Cai, Xuejuan Wan, Haixia Qian, Guanghui Yang
Aza-helicenes are one of the most important series of heterohelicenes; herein, a series of novel aza-helicenes (5H, 6H, 6S, and 8S) were prepared via Bischler–Napieralski cyclization, and the interconversion dynamic process of these aza-helicenes was revealed using density functional theory calculations. The novel nitrogen-doped [6]helicene (6H) possesses a very high interconversion energy barrier
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Solvent-Free Mechanosynthesis of Polysubstituted 1,2-Dihydroquinolines from Anilines and Alkyne Esters J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Hui Xu, Guan-Wu Wang
A novel one-pot reaction of anilines with acetylenedicarboxylate diesters in the presence of boron trifluoride, iodine, and trifluoroacetic acid or methylsulfonic acid has been developed under solvent-free ball-milling conditions, affording a variety of polysubstituted 1,2-dihydroquinolines bearing multiple ester groups in moderate to excellent yields. The present protocol features mild reaction conditions
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Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Yuan Zhang, Tongda Liu, Li Liu, Haiyang Guo, Heyang Zeng, Wei Bi, Guanyinsheng Qiu, Wei Gao, Xin Ran, Long Yang, Guanben Du, Lianpeng Zhang
Here, we report a novel and facile protocol for the synthesis of benz[c,d]indol-2-imines via palladium-catalyzed C–C and C–N coupling of 8-halo-1-naphthylamines with isocyanides in a single step. The reaction features broad substrate scopes and mild conditions, providing an efficient alternative for the construction of antiproliferative agents and BET bromodomain inhibitors. If 0.1 mL of H2O was added
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Visible-Light-Induced Oxyalkylation of 1,2,4-Triazine-3,5(2H, 4H)-diones with Ethers via Oxidative Cross-Dehydrogenative Coupling J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Yushi Tan, Wu Xuekun, Ya-Ping Han, Yuecheng Zhang, Hong-Yu Zhang, Jiquan Zhao
An efficient and convenient method to synthesize 6-oxyalkylated 1,2,4-triazine-3,5(2H, 4H)-diones has been developed via visible-light-induced cross-dehydrogenative coupling reaction between 1,2,4-triazine-3,5(2H, 4H)-diones and ethers with a wide range of functional group tolerance. The present transformation employs the cheap and low-toxic 2-tert-butylanthraquinone as a metal-free photocatalyst and
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Fe-Catalyzed Three-Component Coupling Reaction of α,β,γ,δ-Unsaturated Carbonyl Compounds and Conjugate Dienes with Alkylsilyl Peroxides and Nucleophiles J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Hanbin Lu, Canhua Zhou, Zhe Wang, Terumasa Kato, Yan Liu, Keiji Maruoka
An Fe(OTf)2-catalyzed three-component coupling reaction of α,β,γ,δ-unsaturated carbonyl compounds with alkylsilyl peroxides in the presence of certain heteronucleophiles (ROH and indole) is realized under mild reaction conditions. A variety of α,β,γ,δ-diene carbonyl substrates with different substituents were successfully employable via combination with several different alkylsilyl peroxides. This
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Intermolecular Hydrogen-Bond-Assisted Solid-State Dual-Emission Molecules with Mechanical Force-Induced Enhanced Emission J. Org. Chem. (IF 4.354) Pub Date : 2022-06-21 Xiaohui Wang, Jianyu Zhang, Xiaoyu Mao, Yiwei Liu, Ruikuan Li, Jie Bai, Jun Zhang, Carl Redshaw, Xing Feng, Ben Zhong Tang
Hydrogen bonds not only play a crucial role in the life sciences but also endow molecules with fantastic physical and chemical properties, which help in the realization of their high-tech applications. This work presents an efficient strategy for achieving highly efficient solid-state dual-emission blue emitters with mechanical force-induced enhanced emission properties via intermolecular hydrogen
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Synthesis and Azobenzene Isomerization Investigation of Photoswitchable Glycomacrocycles J. Org. Chem. (IF 4.354) Pub Date : 2022-06-21 Jinbiao Jiao, Stéphane Maisonneuve, Juan Xie
Macrocyclic glycoazobenzenes, as an emerging class of photoswitchable chiral macrocyclic compounds, have shown interesting properties since their discovery in 2017. We have recently employed the azobenzene-ester-linked glycosyl donor–acceptor pairs to study the influence of photoisomerization on intramolecular glycosylation. To continue the investigation on the stereoselectivity aspect of glycosylation
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Visible-Light-Driven Organophotocatalyzed Multicomponent Approach for Tandem C(sp3)–H Activation and Alkylation Followed by Trifluoromethylthiolation J. Org. Chem. (IF 4.354) Pub Date : 2022-06-21 Krishna Gopal Ghosh, Debabrata Das, Sumit Garai, Palasetty Chandu, Devarajulu Sureshkumar
A visible-light-driven organophotocatalyzed multicomponent approach has been developed for tandem direct C(sp3)–H activation and alkylation followed by trifluoromethylthiolation in a one-pot operation. We report a completely metal-free, tandem, three-component approach for the difunctionalization of activated alkenes via the photoinduced radical pathway. This protocol allows the formation of two new
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Fe-BPsalan Complex-Catalyzed Asymmetric [4 + 2] Cycloaddition of Cyclopentadiene with α,β-Unsaturated Heterocycles J. Org. Chem. (IF 4.354) Pub Date : 2022-06-21 Kai-Ge Chen, Hao Lu, Yi-Ming Zhou, Xiao-Long Wan, Hao-Yang Wang, Zhen-Jiang Xu, Hai-Ming Guo, Chi-Ming Che
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Rearrangement of Methylenebis(cyclohexane-1,3-dione) Enols Induced by Mn(III)-Catalyzed Aerobic Oxidation J. Org. Chem. (IF 4.354) Pub Date : 2022-06-21 Yûki Murakami, Kazuki Hisano, Hiroshi Nishino
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Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines J. Org. Chem. (IF 4.354) Pub Date : 2022-06-20 Ankur Maji, Shivangi Gupta, Milan Maji, Sabuj Kundu
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Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles J. Org. Chem. (IF 4.354) Pub Date : 2022-06-20 Karthick Govindan, Alageswaran Jayaram, Tamilselvan Duraisamy, Nian-Qi Chen, Wei-Yu Lin
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Copper-Catalyzed Synthesis of Functionalized Aryl Sulfonamides from Sodium Sulfinates in Green Solvents J. Org. Chem. (IF 4.354) Pub Date : 2022-06-19 Long Yin Lam, King Hong Chan, Cong Ma
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Peculiar Reaction Products and Mechanisms Revisited with Machine Learning-Augmented Computational NMR J. Org. Chem. (IF 4.354) Pub Date : 2022-06-18 Ivan M. Novitskiy, Andrei G. Kutateladze
DU8ML, a fast and accurate machine learning-augmented density functional theory (DFT) method for computing nuclear magnetic resonance (NMR) spectra, proved effective for high-throughput revision of misassigned natural products. In this paper, we disclose another important aspect of its application: correction of unusual reaction mechanisms originally proposed because of incorrect product structures
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Nickel-Catalyzed Decarbonylative Thioetherification of Carboxylic Acids with Thiols J. Org. Chem. (IF 4.354) Pub Date : 2022-06-18 Tianhao Xu, Xingyu Zhou, Xiong Xiao, Yan Yuan, Long Liu, Tianzeng Huang, Chunya Li, Zhi Tang, Tieqiao Chen
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Photocatalyzed Defluorinative Dichloromethylation of α-CF3 Alkenes Using CHCl3 as the Radical Source J. Org. Chem. (IF 4.354) Pub Date : 2022-06-18 Mei-Chun Wu, Yi-Xuan Chen, Ming-Zhi Li, Jun-An Xiao, Zhi-Peng Ye, Jian-Ping Guan, Hao-Yue Xiang, Kai Chen, Hua Yang
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Selective Synthesis of Ketones and Chiral Allylic Alcohols from the Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Mediated by a Transition Metal/Monophosphorus Ligand System J. Org. Chem. (IF 4.354) Pub Date : 2022-06-17 Rui Miao, Jinyong Huang, Yanping Xia, YiFei Wei, Renshi Luo, Lu Ouyang
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Construction of α,β-Diamino Diacid Derivatives with Adjacent Acyclic Tetrasubstituted Stereocenters J. Org. Chem. (IF 4.354) Pub Date : 2022-06-17 Feng Zhou, Qi-Long Hu, Ke-Qiang Hou, Albert S. C. Chan, Xiao-Feng Xiong
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Design of Photosensitive Cobalt Complex Intermediates and Their Application in the Green Syntheses of Molecules Containing the Quinazolin-4(3H)-imine Scaffold J. Org. Chem. (IF 4.354) Pub Date : 2022-06-16 Xianwei Zhang, Tianzhao Wang, Shisheng Cui, Lei Li, Zhibing Zheng, Chunlai Mi, Bin Lin, Xuhong Ren, Xinhua He
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Enhanced Reactivity for Aromatic Bromination via Halogen Bonding with Lactic Acid Derivatives J. Org. Chem. (IF 4.354) Pub Date : 2022-06-16 Sarah I. Baker, Mahshid Yaghoubi, Samantha L. Bidwell, Savannah L. Pierce, Hrant P. Hratchian, Ryan D. Baxter
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Free Radical Promoted Trifluoromethylthiolation of Alkynes to Access SCF3-Containing Dibenzazepines or Dioxodibenzothiazepines J. Org. Chem. (IF 4.354) Pub Date : 2022-06-16 Yingming Ren, Qinqin Yan, Yang Li, Yongjun Gao, Jincan Zhao, Lijun Li, Zhong-Quan Liu, Zejiang Li
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Transition-Metal-Catalyzed Carbonylative Multifunctionalization of Alkynes J. Org. Chem. (IF 4.354) Pub Date : 2022-06-16 Zhiping Yin, Weidong Shi, Xiao-Feng Wu
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Development of Biocompatible Ene-Ligation Enabled by Prenyl-Based β-Caryophyllene with Triazoline/Selectfluor under Physiological Conditions J. Org. Chem. (IF 4.354) Pub Date : 2022-06-16 Sheng Wang, Yuanyuan Li, Hongling Zhou, Li Wang, Rui Wang
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Visible-Light-Promoted Cross Dehydrogenative/Decarboxylative Coupling Cascades of Glycine Ester Derivatives and β-Keto Acids J. Org. Chem. (IF 4.354) Pub Date : 2022-06-15 Chunhui Jiang, Xuefei Sha, Cheng Ni, Wei Qin, Xuejie Zhu, Shan Wang, Xuan Li, Hongfei Lu
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Iron-Promoted Oxidative Alkylation/Cyclization of Ynones with 4-Alkyl-1,4-dihydropyridines: Access to 2-Alkylated Indenones J. Org. Chem. (IF 4.354) Pub Date : 2022-06-15 Fang-Ting Xiong, Bin-Hong He, Yu Liu, Quan Zhou, Jian-Hong Fan
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Chlorahupetenes A–D, Four Eudesmane-Type Sesquiterpenoid Dimer Enantiomers with Two Unusual Carbon Skeletons from Chloranthus henryi Var. hupehensis J. Org. Chem. (IF 4.354) Pub Date : 2022-06-15 Dan-Yang Zhang, Jing-Jing Zhou, Hui Yang, Min Wang, Ya-Nan Wang, Shuai Liu, Zi-Mo Zhang, Peng-Yu Zhuang, Xiao-Xia Wang, Hang Liu
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Trifluoroacetic Acid-Mediated Denitrogenative ortho-Hydroxylation of 1,2,3-Benzotriazin-4(3H)-ones: A Metal-Free Approach J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Kanagaraj Madasamy, Madasamy Hari Balakrishnan, Ramaraju Korivi, Subramaniyan Mannathan
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Visible-Light Photoredox Catalysis in Water J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Camilla Russo, Francesca Brunelli, Gian Cesare Tron, Mariateresa Giustiniano
The use of water in organic synthesis draws attention to its green chemistry features and its unique ability to unveil unconventional reactivities. Herein, literature about the use of water as a reaction medium under visible-light photocatalytic conditions is summarized in order to highlight challenges and opportunities. Accordingly, this Synopsis has been divided into four different sections focused
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Kinetic Resolution of 2-Aryl-4-methylenepiperidines toward Enantioenriched Functionalizable Piperidine Fragments J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Anthony Choi, Anthony J. H. M. Meijer, Ilaria Proietti Silvestri, Iain Coldham
The base n-BuLi with sparteine allows a kinetic resolution of N-Boc-2-aryl-4-methylenepiperidines. The 2,2-disubstituted products and recovered starting materials were isolated with high enantiomeric ratios. From VT-NMR spectroscopy and DFT studies, the rate of rotation of the N-Boc group is fast. Lithiation and trapping of the enantioenriched starting materials gave 2,2-disubstituted piperidines with
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Continuous Flow Technology as an Enabler for Innovative Transformations Exploiting Carbenes, Nitrenes, and Benzynes J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Kian Donnelly, Marcus Baumann
Miniaturization offered by microreactors provides for superb reaction control as well as excellent heat and mass transfer. By performing chemical reactions in microreactors or tubular systems under continuous flow conditions, increased safety can be harnessed which allows exploitation of these technologies for the generation and immediate consumption of high-energy intermediates. This Synopsis demonstrates
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Selective Reduction of Quinolinones Promoted by a SmI2/H2O/MeOH System J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Dengbing Xie, Songlin Zhang
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Asymmetric Cascade Aza-Henry/Lactamization Reaction in the Highly Enantioselective Organocatalytic Synthesis of 3-(Nitromethyl)isoindolin-1-ones from α-Amido Sulfones J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Lorenzo Serusi, Laura Palombi, Giovanni Pierri, Antonia Di Mola, Antonio Massa
The asymmetric synthesis of novel 3-substituted isoindolinones is herein reported. A new cascade reaction was developed that consisted of the asymmetric nitro-Mannich reaction of suitable α-amido sulfones designed from 2-formyl benzoates, followed by the in situ cyclization of the adducts. Very high enantioselectivities, up to 98% ee, and very good yields were obtained in the presence of the readily
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An Environmentally Benign Multicomponent Cascade Reaction of 3-Formylchromones, 2-Naphthols, and Heterocyclic Ketal Aminals: Site-Selective Synthesis of Functionalized Morphan Derivatives J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Ying-Gang Duan, Yi-Hua Chen, Zi-Han Lu, Rong Huang, Sheng-Jiao Yan
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Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3 + 2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(−)-Puraquinonic Acid J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Miho Oga, Yusei Takamatsu, Akihiro Ogura, Ken-ichi Takao
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Unified Total Synthesis of Tetracyclic Diquinane Lycopodium Alkaloids (+)-Paniculatine, (−)-Magellanine, and (+)-Magellaninone J. Org. Chem. (IF 4.354) Pub Date : 2022-06-14 Bing-Bing Huang, Kaiyu Lei, Lin-Rui Zhong, Xiaoliang Yang, Zhu-Jun Yao
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Synthesis of Azepinoindoles via Pd-Catalyzed C(sp2)–H Imidoylative Cyclization Reactions J. Org. Chem. (IF 4.354) Pub Date : 2022-06-13 Jiang Wang, Pinzhuo Ren, Gongping Gu, Zongyou Jiang, Bolin Xiang, Shi Tang, Ai-Qun Jia
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Ruthenium-Catalyzed Pyridine-Directed Aryl C–H Glycosylation with Glycosyl Chlorides J. Org. Chem. (IF 4.354) Pub Date : 2022-06-13 Shaokun Cai, Qikai Sun, Quanquan Wang, Gang He, Gong Chen