TIN TETRACHLORIDE-INDUCED PI-CYCLIZATIONS OF GLYCINE CATION EQUIVALENTS TO SUBSTITUTED PIPECOLIC ACID-DERIVATIVES

被引：47

作者：

ESCH, PM ^{[1
]}

BOSKA, IM ^{[1
]}

HIEMSTRA, H ^{[1
]}

DEBOER, RF ^{[1
]}

SPECKAMP, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON | 1991年 / 47卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)86443-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cationic pi-cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)acetoxyglycine esters induced by tin tetrachloride in dichloromethane are described. Reactions started and quenched with water at -78-degrees-C mainly yield cis-4-hydroxypipecolic esters, whereas reactions quenched after warm-up to room temperature provide trans-4-chloropipecolic esters as major products. A mechanistic scheme is advanced which adequately explains these results. The essentials are a rapid cationic aza-Cope equilibrium of the incipient iminium cation, and participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

引用

页码：4039 / 4062

页数：24

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