HOMOCHIRAL ALPHA,BETA-UNSATURATED GAMMA-LACTAMS - VERSATILE TEMPLATES

被引：45

作者：

RASSU, G

CASIRAGHI, G

SPANU, P

PINNA, L

FAVA, GG

FERRARI, MB

PELOSI, G

机构：

[1] CNR,TECN CHIM AVANZATE,IST APPLICAZ,I-07100 SASSARI,ITALY

[2] CNR,CTR STUDIO STRUTTURIST DIFFRATTOMETR,I-43100 PARMA,ITALY

[3] UNIV PARMA,IST CHIM GEN,I-43100 PARMA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 08期

关键词：

HOMOCHIRAL GAMMA-LACTAMS; HYDROXYLATED PYRROLIDINONES; ASYMMETRIC SYNTHESIS;

D O I：

10.1016/S0957-4166(00)86037-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantiomerically pure crystalline alpha,beta-unsaturated gamma-lactams 4 and 5 have been synthesized by utilizing 2,3-O-isopropylidene-D-glyceraldehyde (3) as chiral source and novel N-tert-butoxycarbonyl-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as four carbon homologative reagent. Unsaturated lactam 4 has been selectively elaborated into hydroxylated pyrrolidiones 7,8, and 11 by stereocontrolled procedures involving conjugate addition of organocuprates, cis-dihydroxylation, and alpha-alkylation via hydrogenation and enolate formation. The absolute stereochemistries of 4 and 5 have been secured by single crystal X-ray analyses.

引用

页码：1035 / 1048

页数：14

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