Oxaziridine-Mediated Ring Expansions of Substituted Cyclobutanones: Synthesis of (-)-γ-Amino-β-Hydroxybutyric Acid (GABOB)
- 1 March 1991
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 21 (5) , 693-701
- https://doi.org/10.1080/00397919108020838
Abstract
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.Keywords
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