Organocatalytic Enantioselective Vinylogous Michael Reaction of Vinylketene Silyl-N,O-Acetals

被引：43

作者：

Basu, Smita ^{[1
]}

Gupta, Vaishali ^{[1
]}

Nickel, Johannes ^{[1
]}

Schneider, Christoph ^{[1
]}

机构：

[1] Univ Leipzig, Inst Organ Chem, D-04103 Leipzig, Germany

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 01期

关键词：

ALPHA; BETA-UNSATURATED GAMMA-BUTYROLACTAM; BIS(OXAZOLINE) COPPER(II) COMPLEXES; ALDOL REACTIONS; SILYL GLYOXYLATES; NATURAL-PRODUCTS; NITROALKENES; CATALYSIS; ALDEHYDES; CONSTRUCTION; BUTENOLIDES;

D O I：

10.1021/ol403275k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective vinylogous Michael reaction of vinylketene silyl N,O-acetals derived from alpha,beta-unsaturated N-acyl pyrroles and a broad range of alpha,beta-unsaturated aldehydes proceeds with good regio-, diastereo-, and enantioselectivity when the Hayashi-Jorgensen diphenylprolinolsilylether was employed as a chiral organocatalyst. Products were obtained in generally good yields and as single stereoisomers after chromatographic purification with very high optical purity. They were easily derivatized into a set of useful synthetic building blocks.

引用

页码：274 / 277

页数：4

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