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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