ASYMMETRIC ALDOL REACTIONS OF ACHIRAL 2-PHENYLSULFANYL ALDEHYDES WITH SMALL-SIZED AND MEDIUM-SIZED CARBOCYCLIC RINGS - THE SYNTHESIS OF HOMOCHIRAL SPIROCYCLIC LACTONES, PYRROLIDINES AND TETRAHYDROFURANS

被引：16

作者：

CHIBALE, K ^{[1
]}

WARREN, S ^{[1
]}

机构：

[1] UNIV CAMBRIDGE, CHEM LAB, CAMBRIDGE CB2 1EW, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 19期

关键词：

D O I：

10.1039/p19950002411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral boron enolates based on the 1,3-oxazolidin-2-one auxiliary react with achiral 1-phenylsulfanylcycloalkanecarbaldehydes in anti- and syn-selective aldol processes to give the corresponding aldol products with moderate to excellent levels of diastereo- and enantio-control. Stereospecific cyclisation via an asymmetric episulfonium (thiiranium) ion leads to optically pure spirocyclic compounds in high chemical yields.

引用

页码：2411 / 2418

页数：8

共 26 条

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