N-Heterocyclic Carbene-Catalyzed [3+4] Annulation of Enals and Alkenyl Thiazolones: Enantioselective Synthesis of Thiazole-Fused ε-Lactones

被引：53

作者：

Liang, Zhi-Qin ^{[1
]}

Yi, Liang ^{[1
]}

Chen, Kun-Quan ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 11期

基金：

美国国家科学基金会;

关键词：

BOND-FORMING REACTIONS; DIELS-ALDER REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; COOPERATIVE CATALYSIS; BENZOIN CONDENSATION; GAMMA-BUTYROLACTONES; BETA-HYDROXYLATION; STETTER REACTIONS; 4+2 CYCLOADDITION; MICHAEL ADDITION;

D O I：

10.1021/acs.joc.6b00313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bifunctional N-heterocyclic carbene catalyzed [3 + 4] annulation of enals and 5-alkenyl thiazolones was developed, giving, the corresponding thiazole-fused e-lactones in high yields with excellent diastereoselectivties and enantioselectivities. The thiazole-fused e-lactone could be isomerized to the spirocyclic thiazolone-cyclopentanone without erosion of enantioselectivity.

引用

页码：4841 / 4846

页数：6

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