ASYMMETRIC LEWIS ACID-CATALYZED ADDITION OF A KETENE DITHIOACETAL TO A CHIRAL BICYCLIC LACTAM - FORMATION OF CYCLOBUTANOPYRROLIDINONES - A NEW CLASS OF GABA DERIVATIVES

被引：22

作者：

MEYERS, AI

TSCHANTZ, MA

BRENGEL, GP

机构：

[1] Department of Chemistry, Colorado State University, Fort Collins

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 14期

关键词：

D O I：

10.1021/jo00119a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Additions to unsaturated chiral lactams 8 using methylenedithiolane, gave very high endo-selectivity of the cyclobutane adducts (2 + 2 addition) 13, 16. Removal of the phenylglycinol auxiliary by reductive cleavage produced the title compound (+)-20 in very high (>99%) enantiomeric excess. Absolute stereochemistry of the cyclobutanopyrrolidinone, containing three contiguous stereocenters, was confirmed by X-ray crystallography.

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页码：4359 / 4362

页数：4

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