Asymmetric Umpolung (3+2) Cycloadditions of Iminoesters with α,β-Unsaturated-2-acyl Imidazoles for the Synthesis of Substituted Pyrrolidines,Organic Letters

当前位置： X-MOL 学术 › Org. Lett. › 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 Umpolung (3+2) Cycloadditions of Iminoesters with α,β-Unsaturated-2-acyl Imidazoles for the Synthesis of Substituted Pyrrolidines
Organic Letters ( IF 4.9 ) Pub Date : 2022-07-29 , DOI: 10.1021/acs.orglett.2c01438
Mamta Gill ₁ , Arko Das ₁ , Vinod K Singh ₁

Affiliation

An enantioselective (3+2) cycloaddition reaction of iminoesters occurring with opposite regioselectivity is reported. This reaction provides chiral polysubstituted pyrrolidines with high enantioselectivities (up to 97%), diastereoselectivities (>20:1), and yields (up to 99%). Interestingly, changing the alpha-substituents of the iminoesters from an aryl to an aliphatic (benzyl) group or hydrogen resulted in the formation of normal (3+2) cycloaddition products, also in excellent enantioselectivities.

中文翻译：

亚胺酯与 α,β-不饱和-2-酰基咪唑的不对称 Umpolung (3+2) 环加成用于合成取代吡咯烷

报道了以相反的区域选择性发生的亚氨基酯的对映选择性 (3+2) 环加成反应。该反应提供了具有高对映选择性（高达 97%）、非对映选择性（>20:1）和产率（高达 99%）的手性多取代吡咯烷。有趣的是，将亚氨基酯的 α-取代基从芳基变为脂肪族（苄基）基团或氢会导致形成正常的 (3+2) 环加成产物，同时具有出色的对映选择性。

更新日期：2022-07-29

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11