STEREOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANES FROM 2-PHENYLSULFONYL-1,3-CYCLOHEXADIENES AND KETONE ENOLATES OR NITRILE ANION

被引：7
作者：
ERICSSON, AM
PLOBECK, NA
BACKVALL, JE
机构：
来源：
ACTA CHEMICA SCANDINAVICA | 1994年 / 48卷 / 03期
关键词：
D O I：
10.3891/acta.chem.scand.48-0252
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Michael addition of ketone enolates to 2-(phenylsulfonyl)-1,3-cyclohexadienes and subsequent cyclization affords vinylcyclopropanes in a highly stereoselective manner. In this process the enolate anion of the adduct displaces the allylic phenylsulfonyl group. The analogous reaction between the anion of benzyl cyanide and 2-(phenylsulfonyl)-1,3-cyclohexadiene afforded the corresponding vinylcyclopropane. An attempted synthesis of sesquicarene led to the sesquicarene derivative 3,endo-7-dimethyl-exo-7-(4-hydroxy-4-methylpentanoyl)-2-norcarene.
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页码：252 / 257
页数：6
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