C,C COUPLING WITH SULFUR-STABILIZED CARBANIONS .2. REACTIONS OF THE 2-(METHYLTHIO)THIOLANE CARBANION WITH ELECTROPHILES

被引：4

作者：

BOGE, A ^{[1
]}

BRUNCK, JS ^{[1
]}

SCHWAR, G ^{[1
]}

VOSS, J ^{[1
]}

机构：

[1] UNIV HAMBURG,INST ORGAN CHEM,MARTIN LUTHER KING PL 6,W-2000 HAMBURG 13,GERMANY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 07期

关键词：

THIOACETALS; SEMICYCLIC; CARBANIONS; ALKYLATION; HYDROXYALKYLATION; DIASTEREOSELECTIVITY; THIOLANES;

D O I：

10.1002/cber.19921250720

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ,,semicyclic'' thioacetal 2-(methylthio)thiolane (4) is easily prepared from thiolane (tetrahydrothiophene). It is readily deprotonated by butyllithium to give the lithium derivative 5, which reacts with alkyl halides, saturated and alpha,beta-unsaturated carbonyl compounds, and benzonitrile to form the alkyl derivatives 6, carbinols 7, allyl alcohols 8, and - after hydrolysis - the ketone 9. The diastereoselectivity of the C,C coupling reaction is discussed.

引用

页码：1641 / 1646

页数：6

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