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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