ORGN 31 |
| Cinchona Alkaloids catalyze the enantioselective Mannich reaction of stabilized anions with acyl imines. The reaction conditions have been developed to employ acyl imines and acyl imine precursors, α-amido sulphones. The reaction requires 10 mol% of cinchona alkaloid catalyst. We have obtained the reaction products in good yields, high enantioselectivities, and in diastereoselectivities that range from 1:1 to >95:5. The cinchonine-catalyzed reactions provide practical access to highly functionalized building blocks. The reaction of β-keto esters with acyl imines affords intermediates for synthesis of chiral dihydropyrimidones, a class of compounds pharmacologically rich in diverse biological activity. |
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Asymmetric Reactions and Syntheses
8:00 AM-12:20 PM, Sunday, 10 September 2006 Moscone Center -- Room 131, Oral
Division of Organic Chemistry |