首页   按分类浏览 期刊浏览 卷期浏览 Oxaziridine-Mediated Ring Expansions of Substituted Cyclobutanones: Synthesis of (-)-&#...
Oxaziridine-Mediated Ring Expansions of Substituted Cyclobutanones: Synthesis of (-)-γ-Amino-β-Hydroxybutyric Acid (GABOB)

 

作者: Jeffrey Aubé,   Yuguang Wang,   Shomir Ghosh,   KendraL. Langhans,  

 

期刊: Synthetic Communications  (Taylor Available online 1991)
卷期: Volume 21, issue 5  

页码: 693-701

 

ISSN:0039-7911

 

年代: 1991

 

DOI:10.1080/00397919108020838

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

The synthesis and photochemical rearrangement chemistry of oxaziridnes derived from 3-benzyloxy- and 3-phenylcyclobutanone were examined. The oxaziridines were prepared by condensation of the ketones with α-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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