Organocatalytic asymmetric synthesis of 5-(trialkylsilyl)cyclohex-2-enones and the transformation into useful building blocks

被引：36

作者：

Bolze, Patrick ^{[1
]}

Dickmeiss, Gustav ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Danish Natl Res Fdn Ctr Catalysis, DK-8000 Aarhus C, Denmark

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 17期

基金：

新加坡国家研究基金会;

关键词：

D O I：

10.1021/ol801392d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple organocatalytic approach to highly attractive chiral building blocks is presented. By the reaction of beta-ketoesters with alpha,beta-unsaturated aldehydes using a chiral TINS-protected prolinol as the catalyst, optically active 5-(trialkylsilyl)cyclohex-2-enones are formed in good yields and with 98-99% ee. The applications of 5-(trialkylsilyl)cyclohex-2-enones for the formation of 5-(hydroxy)cyclohex-2-enones and the A-ring of 19-nor-1 alpha,25-dihydroxyvitamin D-3 are also presented.

引用

页码：3753 / 3756

页数：4

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