LEWIS ACID-CATALYZED MICHAEL-TYPE ADDITION - A NEW REGIOSELECTIVE AND DIASTEREOSELECTIVE ANNULATION METHOD USING METHYL VINYL KETONE

被引：63

作者：

DUHAMEL, P ^{[1
]}

DUJARDIN, G ^{[1
]}

HENNEQUIN, L ^{[1
]}

POIRIER, JM ^{[1
]}

机构：

[1] IRCOF,F-76134 MONT ST AIGNAN,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 03期

关键词：

D O I：

10.1039/p19920000387

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new annulation method is presented, involving a boron trifluoride catalysed Michael addition of trialkylsilyl enol ethers to methyl vinyl ketone (MVK) in the presence of a hydroxylic compound. This methodology allows regiospecific 3-oxobutylation of either of the two isomeric enol ethers of mono or di-substituted cyclanones. Octalones 2d, e and hydrindenones 17 with the two alkyl groups in a cis relationship can thus be specifically obtained. This method has been applied to a short and efficient preparation of (+/-)-dehydrofukinone 10.

引用

页码：387 / 396

页数：10

共 65 条

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