OXAZIRIDINE-MEDIATED RING EXPANSIONS OF SUBSTITUTED CYCLOBUTANONES - SYNTHESIS OF (-)-GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID (GABOB)

被引：28

作者：

AUBE, J

WANG, YG

GHOSH, S

LANGHANS, KL

机构：

[1] Department of Medicinal Chemistry, The University of Kansas, Lawrence

来源：

SYNTHETIC COMMUNICATIONS | 1991年 / 21卷 / 05期

关键词：

D O I：

10.1080/00397919108020838

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and photochemical rearrangement chemistry of oxaziridines derived from 3-benzyloxy- and 3-phenylcyclobutanone were examined. The oxaziridines were prepared by condensation of the ketones with alpha-methylbenzylamine followed by oxidation. Photolysis at 254 nm afforded good yields of readily separable lactams; 4-benzyloxy-pyrrolidin-2-one obtained in this way was converted to 4-amino-3-hydroxybutanoic acid (GABOB) by catalytic hydrogenolysis followed by acid hydrolysis.

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页码：693 / 701

页数：9

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