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Enantioselective Processes. Reaction of Optically Active Amines with Photochemically Generated Ketenes
Schultz, Arthur G.,Kulkarni, Yashwant S.
, p. 5202 - 5206 (2007/10/02)
The diastereoselectivity of the reaction of d- and l-ephedrine with ketenes photochemically generated from 6-(2-oxopropyl)-2,4,6-trimethyl-2,4-cyclohexadien-1-one (1a), 6-(2-oxopropyl)-2,6-dimethyl-2,4-cyclohexadien-1-one (1b), and 6-acetoxy-2,4,6-trimethyl-2,4-cyclohexadien-1-one (3a) is described.Configurational assignments at C(2) in the major products 5a and 6 resulting from irradiation of 1a in the presence of d-ephedrine and l-ephedrine, respectively, were made by chemical degradation and correlation studies with (S)-(+)-3-hydroxy-2-methylpropanoic acid (7a).
