Organocatalytic and Electrophilic Approach to Oxindoles with C3-Quaternary Stereocenters

被引：103

作者：

Peng, Jing ^{[1
]}

Huang, Xin ^{[1
]}

Cui, Hai-Lei ^{[1
]}

Chen, Ying-Chun ^{[1
,2
]}

机构：

[1] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Key Lab Drug Targeting & Drug Delivery Syst Educ, Chengdu 610041, Peoples R China

[2] Sichuan Univ, W China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 19期

基金：

中国国家自然科学基金;

关键词：

BAYLIS-HILLMAN CARBONATES; ALLYLIC ALKYLATION; ENANTIOSELECTIVE CONSTRUCTION; STEREOSELECTIVE CONSTRUCTION; QUATERNARY STEREOCENTERS; SPIROCYCLIC OXINDOLES; GAMMA-BUTENOLIDES; SUBSTITUTION; DERIVATIVES; ACETATES;

D O I：

10.1021/ol101668z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Lewis base-catalyzed asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates derived from isatins has been investigated, which provides an electrophilic pathway to access oxindoles bearing C3-quaternary stereocenters. Excellent diastereoselectivity and high enantioselectivity have been obtained in the vinylogous functionalization of alpha,alpha-dicyanoolefin nucleophiles, giving multifunctional products with vicinal quaternary and tertiary chiral carbon centers.

引用

页码：4260 / 4263

页数：4

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