Organocatalytic Enantioconvergent Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8-Addition to aza-para-Quinone Methides

被引：74

作者：

Chen, Min ^{[1
,2
]}

Qian, Deyun ^{[1
,2
]}

Sun, Jianwei ^{[1
,2
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Clear Water Bay, Hong Kong, Peoples R China

[2] Hong Kong Univ Sci & Technol, Shenzhen Res Inst, Kowloon, Clear Water Bay, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

基金：

中国国家自然科学基金;

关键词：

BRONSTED ACID; 1,6-CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITIONS; CONSTRUCTION; ACTIVATION; ALKYLATION; POLYMERS; ALCOHOLS; ENAMIDES;

D O I：

10.1021/acs.orglett.9b03224

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to the well-explored quinone methides (QMs) and aza-ortho-QMs, aza-para-QMs have been rarely studied in terms of their asymmetric transformations. Herein, a highly efficient enantioconvergent asymmetric 1,8-addition of aza-para-QMs is described. Featuring remarkable remote stereocontrol, this reaction provides expedient access to chiral tetrasubstituted allenes bearing an adjacent all-carbon quaternary stereocenter with high enantioselectivity and diastereoselectivity.

引用

页码：8127 / 8131

页数：5

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