Highly Enantioselective Trapping of Carboxylic Oxonium Ylides with Imines for Direct Assembly of Enantioenriched γ-Butenolides  

作　　者：Dan Zhang Xin Wang Mengchu Zhang Zhenghui Kang Guolan Xiao Xinfang Xu Wenhao Hu 

机构地区：[1]Guangdong Key Laboratory of Chiral Molecule and Drug Discovery,School of Pharmaceutical Sciences,Sun Yat-Sen University,Guangzhou 510006

出　　处：《CCS Chemistry》2020年第4期432-439,共8页中国化学会会刊（英文）

基　　金：supported by National Natural Science Foundation of China(no.21901259);Guangdong Basic and Applied Basic Research Foundation(no.2020A1515011116);the Program for Guangdong Introducing Innovative and Entrepreneurial Teams(no.2016ZT06Y337);the National Science&Technology Major Project“Key New Drug Creation and Manufacturing Program”of China(no.2018ZX09711002-006).

摘　　要：Enantioenrichedγ-butenolides are valuable structural cores in many pharmaceuticals and natural products,but their direct and catalytically asymmetric assembly remains rare.Here,we report an efficient,atom-economic synthetic strategy for enantioenrichedγ-butenolides via a unique enantioselective reaction of cyclopropene carboxylic acids with imines under the synergistic catalysis of Rh2(esp)2/chiral Brønsted acid system.The reaction involved trapping of carboxylic oxonium ylides,generated from cyclopropene carboxylic acids,which presented as the first asymmetric trapping reactive intermediate in the process.

关 键 词：CYCLOPROPENES vinyl CARBENES YLIDES asymmetric catalysis γ-butenolides 

分 类 号：O62[理学—有机化学]