Enantioselective Cyclopropanation/[1,5]-Hydrogen Shift to Access Rauhut-Currier Product

被引：7
|
作者：
Kim, Seung Tae [1 ]
Pandit, Rameshwar Prasad [1 ]
Yun, Jaesook [1 ]
Ryu, Do Hyun [1 ]
机构：
[1] Sungkyunkwan Univ, Dept Chem, Suwon 16419, South Korea
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 01期
基金：
新加坡国家研究基金会;
关键词：
ASYMMETRIC-SYNTHESIS; DIAZOESTERS; DERIVATIVES; CONSTRUCTION; QUATERNARY; INSERTION; ESTERS;
D O I：
10.1021/acs.orglett.0c03937
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Michael addition initiated cyclopropanation/[1,5]-hydrogen shift has been developed for the enantioselective synthesis of Rauhut-Currier products. The reaction of alpha-alkyl diazoesters and in situ generated o-quinone methides proceeds in the presence of chiral oxazaborolidinium ion, providing Z-stereocontrolled Rauhut-Currier products in high yields (up to 96%) with excellent Z/E selectivities (>20:1) and enantioselectivities (up to >99% ee). The synthetic utility was illustrated by conversion of the product to 3,4-dihydrocoumarins with two adjacent chiral stereocenters.
引用
收藏
页码：213 / 217
页数：5
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