Mukaiyama-Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17-C28 Fragment of Pectenotoxins

被引：65

作者：

Kemppainen, Eeva K.

Sahoo, Gokarneswar

Valkonen, Arto

Pihko, Petri M. ^{[1
]}

机构：

[1] Univ Jyvaskyla, Dept Chem, FIN-40014 Jyu, Finland

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 04期

基金：

芬兰科学院;

关键词：

DIELS-ALDER REACTION; ASYMMETRIC SYNTHESES; RING-SYSTEM; PART II; IDENTIFICATION; SPIROKETALS; EPOXIDATION; STRATEGY; SEGMENT; ACCESS;

D O I：

10.1021/ol203486p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.

引用

收藏

页码：1086 / 1089

页数：4

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