Synthetic Communications p. 693 - 701 (1991)
Update date:2022-08-03
Topics:
Aube
Wang
Ghosh
Langhans
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.
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(1981)