Oxazole–Carbonyl photocycloadditions: selectivity pattern and synthetic route to erythro α-amino, β-hydroxy ketonesRegarded as Part 10 of the series ‘Stereoselectivity of Triplet Photocycloadditions’, Part 9: A. G. Griesbeck and M. Fiege, in Molecular and Supramolecular Photochemistry, ed. V. Ramamurthy and K. S. Schanze, Marcel Dekker, New York, 2000, vol. 6, in press.

Abstract

The photocycloaddition of aliphatic and aromatic aldehydes with 2,4,5-trimethyloxazole proceeds highly regio- and diastereoselectively to give bicyclic oxetanes; hydrolytic cleavage of these adducts gives selectively erythro α-amino, β-hydroxy methyl ketones.