1259502-07-2Relevant academic research and scientific papers
Diastereoselective reduction of chiral N-tosyl-2-benzoyl-1,3-oxazine derived from (1R)-(+)-camphor
Ko, Kwang-Youn,Yun, Hoseop
, p. 2351 - 2359 (2011/03/23)
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. The Japan Institute of Heterocyclic Chemistry.
