STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED ALPHA-IODOAMIDES - SYNTHESIS OF ENANTIOPURE PYRROLIDINES AND TRANSITION-STATE MODELING

被引：34

作者：

BELVISI, L ^{[1
]}

GENNARI, C ^{[1
]}

POLI, G ^{[1
]}

SCOLASTICO, C ^{[1
]}

SALOM, B ^{[1
]}

VASSALLO, M ^{[1
]}

机构：

[1] UNIV MILAN,CNR,CTR STUDIO SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1992年 / 48卷 / 19期

关键词：

D O I：

10.1016/S0040-4020(01)88474-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical-mediated cyclization of norephedrine derived alpha-iodoamides 1 was found to be highly stereoselective (> 97.3) favouring diastereoisomer 2. Bicyclic lactams 2 were transformed in high yields into enantiomerically pure pyrrolidines 10. Transition state modelling with a force field developed ad hoc nicely predicts the stereochemical results.

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页码：3945 / 3960

页数：16

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