Oxaziridine-mediated ring expansions of substituted cyclobutanones: Synthesis of (-)-γ-amino-β-hydroxybutyric acid (GABOB)

Article abstract of DOI:10.1080/00397919108020838

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 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.

Full text of DOI:10.1080/00397919108020838

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Synthetic Communications: An
International Journal for Rapid
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Organic Chemistry
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Oxaziridine-Mediated Ring
Expansions of Substituted
Cyclobutanones: Synthesis of
(-)-γ-Amino-β-Hydroxybutyric
Acid (GABOB)
Jeffrey Aubé a , Yuguang Wang a , Shomir Ghosh a &
Kendra L. Langhans a
a Department of Medicinal Chemistry , The
University of Kansas Lawrence , Kansas, 66045-2500
Published online: 23 Sep 2006.
To cite this article: Jeffrey Aubé , Yuguang Wang , Shomir Ghosh & Kendra L.
Langhans (1991) Oxaziridine-Mediated Ring Expansions of Substituted Cyclobutanones:
Synthesis of (-)-γ-Amino-β-Hydroxybutyric Acid (GABOB), Synthetic Communications:
An International Journal for Rapid Communication of Synthetic Organic Chemistry,
21:5, 693-701, DOI: 10.1080/00397919108020838
To link to this article: http://dx.doi.org/10.1080/00397919108020838
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