ORGN 98 |
| Daniel R. Clark and William F. Bailey. Department of Chemistry, University of Connecticut, 55 N Eagleville Rd., Unit 3060, Storrs, CT 06269-3060 |
| The diastereofacial selectivity of the reaction of various metal hydrides and Grignard reagents with 2-keto-4-methyl-1,3-dioxanes 1 has been investigated. Diastereoselectivities in excess of 90:10 favoring formation of alcohol 2 are observed for additions involving metal hydrides and Grignard reagents that are capable of reasonably strong coordination with the carbonyl oxygen and the dioxane oxygen remote from the 4-methyl group. Application of this simple methodology to the enantioselective preparation of a-hydroxy acids will be discussed.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |