N-Heterocyclic Carbene Catalyzed Formal [3+2] Annulation Reaction of Enals: An Efficient Enantioselective Access to Spiro-Heterocycles

被引：170

作者：

Guo, Chang ^{[1
]}

Schedler, Michael ^{[1
]}

Daniliuc, Constantin G. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Organ Chem Inst, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 38期

关键词：

asymmetric synthesis; enals; N-heterocyclic carbenes; organocatalysis; spiro-heterocycles; CARBON QUATERNARY STEREOCENTERS; GAMMA-BUTYROLACTONES; STEREOSELECTIVE-SYNTHESIS; HOMOENOLATE ADDITIONS; ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; COOPERATIVE CATALYSIS; CONJUGATE UMPOLUNG; INDOLE ALKALOIDS; BREVIANAMIDE-B;

D O I：

10.1002/anie.201405381

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective N-heterocyclic carbene (NHC) catalyzed formal [3+2] annulation of alpha, beta-unsaturated aldehydes with azaaurones or aurone generating spiro-heterocycles has been developed. The protocol represents a unique NHC-activation-based approach to access spiro-heterocyclic derivatives bearing a quaternary stereogenic center with high optical purity (up to 95% ee).

引用

页码：10232 / 10236

页数：5

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