FIRST DIELS-ALDER REACTIONS OF ENANTIOMERICALLY PURE 1-P-TOLYLSULFINYL DIENES - STRAIGHTFORWARD ACCESS TO CYCLOHEXENOLS THROUGH TANDEM CYCLOADDITION [2,3]-SIGMATROPIC REARRANGEMENT

被引：75

作者：

ARCE, E ^{[1
]}

CARRENO, MC ^{[1
]}

CID, MB ^{[1
]}

RUANO, JLG ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM C1,E-28049 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 12期

关键词：

D O I：

10.1021/jo00091a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric Diels-Alder reactions of (R)-1-(p-tolylsulfinyl)-1,3-butadienes 3a-c with N-methylmaleimide (NMM) have been explored. The cycloadditions are stereospecific: only one endo adduct is formed, the pi-facial diastereoselectivity being controlled by the sulfoxide both in thermal and catalytic conditions. The in situ cycloaddition/sulfoxide sulfenate [2,3]-sigmatropic rearrange ment starting from chiral 3a-e in the presence of an excess of NMM, which acts as thiophilic agent, provides a convenient one-step access to enantiomerically pure and all-cis functionalized cyclohexenols (-)-5a-c.

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页码：3421 / 3426

页数：6

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