STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED O-BROMOBENZAMIDES - ENANTIOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES

被引：24

作者：

BELVISI, L ^{[1
]}

GENNARI, C ^{[1
]}

POLI, G ^{[1
]}

SCOLASTICO, C ^{[1
]}

SALOM, B ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(00)82347-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Radical-mediated cyclization of norephedrine derived o-bromobenzamide 5 was found to be fairly stereoselective (85:15)favouring diastereoisomer trans-6. Tricyclic delta-lactams 6 were transformed in high yield into enantiomerically enriched (R)-1,2,3,4-tetrahydro-2,4-dimethylisoquinoline 8. Transition state modelling with a force field developed ad hoc (see also: Belvisi, L. et al. Tetrahedron 1992, 48, 3945) nicely predicts the stereochemical results.

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页码：273 / 280

页数：8

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