当前位置: X-MOL 学术Chem. Rec. › 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.)
Two Decades of Progress in the Asymmetric Intramolecular aza-Michael Reaction
The Chemical Record ( IF 6.6 ) Pub Date : 2021-08-20 , DOI: 10.1002/tcr.202100161
María Sánchez-Roselló 1 , Marcos Escolano 1 , Daniel Gaviña 1 , Carlos Del Pozo 1
Affiliation  

The asymmetric intramolecular aza-Michael reaction (IMAMR) is a very convenient strategy for the generation of heterocycles bearing nitrogen-substituted stereocenters. Due to the ubiquitous presence of these skeletons in natural products, the IMAMR has found widespread applications in the total synthesis of alkaloids and biologically relevant compounds. The development of asymmetric versions of the IMAMR are quite recent, most of them reported in this century. The fundamental advances in this field involve the use of organocatalysts. Chiral imidazolidinones, diaryl prolinol derivatives, Cinchone-derived primary amines and quaternary ammonium salts, and BINOL-derived phosphoric acids account for the success of those methodologies. Moreover, the use of N-sulfinyl imines with a dual role, as nitrogen nucleophiles and as chiral auxiliaries, appeared as a versatile mode of performing the asymmetric IMAMR.

中文翻译:

不对称分子内氮杂-迈克尔反应的两个十年进展

不对称分子内氮杂-迈克尔反应 (IMAMR) 是一种非常方便的生成带有氮取代立体中心的杂环的策略。由于这些骨架在天然产物中无处不在,IMAMR 在生物碱和生物相关化合物的全合成中得到了广泛的应用。IMAMR 的不对称版本的开发是最近才出现的,其中大部分是在本世纪报道的。该领域的基本进展涉及有机催化剂的使用。手性咪唑烷酮、二芳基脯氨醇衍生物、Cinchone衍生的伯胺和季铵盐以及 BINOL 衍生的磷酸是这些方法学成功的原因。此外,使用N具有双重作用的-亚磺酰基亚胺,作为氮亲核试剂和作为手性助剂,作为进行不对称 IMAMR 的通用模式出现。
更新日期:2021-08-20
down
wechat
bug