2,3-Dihydroimidazo[1,2-a]pyridines: a new class of enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols |
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Authors: | Birman Vladimir B Uffman Eric W Jiang Hui Li Ximin Kilbane Corey J |
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Affiliation: | Department of Chemistry, Washington University, One Brookings Drive, St. Louis, Missouri 63130, USA. birman@wustl.edu |
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Abstract: | The long-known, but previously unexplored 2,3-dihydroimidazo[1,2-a]pyridine (DHIP) has been shown to be a competent acyl transfer catalyst. Its chiral 2-phenyl derivatives obtainable in two steps from commercially available starting materials have proved to be effective acylation catalysts, giving high levels of enantioselectivity (s = 20-85) in kinetic resolution of secondary benzylic alcohols. A transition state model explaining the observed selectivity has been proposed. |
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