CHIROSPECIFIC SYNTHESIS OF TRANS-2,5-DISUBSTITUTED PYRROLIDINES VIA STEREOSELECTIVE ADDITION OF ORGANOCOPPER REAGENTS TO N-ACYLIMINIUM IONS

被引：80

作者：

WISTRAND, LG

SKRINJAR, M

机构：

[1] Division of Organic Chemistry 3, University of Lund, Chemical Center, S-221 00 Lund

来源：

TETRAHEDRON | 1991年 / 47卷 / 4-5期

关键词：

D O I：

10.1016/S0040-4020(01)87047-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the N-acyliminium ion precursor 1a (derived from S-proline via anodic methoxylation) with RCu in the presence of BF3.Et2O gives preferentially the trans adducts 2 (trans:cis greater-than-or-equal-to 96:4). Using such a procedure, a general synthetic route to (2R, 5R)-trans-2,5-dialkylpyrrolidines has been developed, as exemplified by the chirospecific syntheses of the ant feromones trans 5-butyl-2-heptylpyrrolidine (10a), trans-5-ethyl-2-heptylpyrrolidine (10b) and trans-5-heptyl-2-(5-hexenyl)pyrrolidine (10c).

引用

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页码：573 / 582

页数：10

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