当前位置: X-MOL 学术Adv. Synth. Catal. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Asymmetric Hydrolytic and Aminolytic Kinetic Resolution of Racemic Epoxides using Recyclable Macrocyclic Chiral Cobalt(III) Salen Complexes
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2017-11-16 , DOI: 10.1002/adsc.201700788
Rajkumar Tak 1, 2 , Manish Kumar 1 , Tusharkumar Menapara 1, 2 , Naveen Gupta 1, 2 , Rukhsana I. Kureshy 1, 2 , Noor-ul H. Khan 1, 2 , E. Suresh 2, 3
Affiliation  

New chiral macrocyclic cobalt(III) salen complexes were synthesized and used as catalyst for the asymmetric kinetic resolution (AKR) of terminal epoxides and glycidyl ethers with aromatic/aliphatic amines and water as nucleophiles. This is the first occasion where a Co(III) salen complex demonstrated its ability to catalyze AKR as well as hydrolytic kinetic resolution (HKR) reactions. Excellent enantiomeric excesses of the epoxides, the corresponding amino alcohols and diols (upto 99%) with quantitative yields were achieved by using the chiral Co(III) salen complexes in dichloromethane at room temperature. This protocol was further extended for the synthesis of two important drug molecules, i.e., (S)‐propranolol and (R)‐naftopidil. The catalytic system was also explored for the synthesis of chirally pure diols and chiral cyclic carbonates using carbon dioxide as a greener renewable C1 source. The catalyst was recycled for upto 5 catalytic cycles with retention of enantioselectivity.

中文翻译:

使用可回收的大环手性钴(III)Salen配合物的外消旋环氧化合物的不对称水解和氨基酸分解动力学

合成了新的手性大环钴(III)salen络合物,并用作端环氧化物和缩水甘油醚与芳香族/脂肪族胺和水为亲核试剂的不对称动力学拆分(AKR)的催化剂。这是Co(III)salen配合物首次证明其催化AKR以及水解动力学拆分(HKR)反应的能力。通过在室温下在二氯甲烷中使用手性Co(III)salen络合物,可实现定量的优异环氧化物,相应的氨基醇和二醇(至多99%)的出色的对映异构体过量。该方案进一步扩展为合成两个重要的药物分子,即(S)-普萘洛尔和(R)萘哌地尔。还探索了使用二氧化碳作为绿色可再生C 1来源合成手性纯二醇和手性环状碳酸酯的催化体系。在保持对映选择性的情况下,将催化剂循环使用多达5个催化循环。
更新日期:2017-11-16
down
wechat
bug