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Note | Regular issue | Vol 81, No. 10, 2010, pp.2351-2359
Published online, 25th August, 2010
DOI: 10.3987/COM-10-12016
Diastereoselective Reduction of Chiral N-Tosyl-2-benzoyl-1,3-oxazine Derived from (1R)-(+)-Camphor

Kwang-Youn Ko* and Hoseop Yun

*Department of Chemistry, Ajou University, 5 Wonchun-Dong, Youngtong-Gu, Suwon 443-749, Korea


The stereochemistry of reduction of chiral N-tosyl-2-benzoyl-1,3-oxazine prepared by condensation of 1,3-amino alcohol derived from (1R)-(+)-camphor with phenylglyoxal was investigated using various reducing agents. Based on X-ray crystallography, 2-benzoyl group in 1,3-oxazine ring was situated in the axial position. High diastereoselectivity observed in the hydride reduction can be explained by a chelate model where N-tosyl oxygen atom takes part in chelation rather than ring oxygen atom.