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Highly Diastereoselective Additions to Chiral α-Keto Acetals

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journal contribution
posted on 22.08.1997, 00:00 by Kauser M. Akhoon, David C. Myles
A general synthesis of (4R*,5R*)-2-acyl-4,5-diphenyl-1,3-dioxolanes and the addition of alkylmagnesium bromides to these compounds is described. The addition reactions occur with high diastereoselectivity (typical selectivity ca. 90:10). An example addition reaction carried out on an optically active acetal proves the sense of asymmetric induction for addition of organomagnesium reagents to these α-keto acetals. An explanation of the mechanism of asymmetric induction is given.