FORMIC ACID-INDUCED PI-CYCLIZATION OF GLYCINE CATION EQUIVALENTS TO SUBSTITUTED PIPECOLIC ACID-DERIVATIVES

被引：34

作者：

ESCH, PM ^{[1
]}

DEBOER, RF ^{[1
]}

HIEMSTRA, H ^{[1
]}

BOSKA, IM ^{[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)86444-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formic acid-mediated cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)-acetoxyglycine esters are described. The major reaction products are 4-formyloxypipecolic acid derivatives, formed with low stereoselectivity at C-4. The several subtle features of the cyclization process are satisfactorily explained by a mechanism involving (1) a rapid cationic aza-Cope rearrangement of the incipient iminium ion and (2) participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

引用

页码：4063 / 4076

页数：14

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