Highly stereoselective oxy-michael additions to beta,gamma-unsaturated alpha-keto esters: rapid enantioselective synthesis of 3-hydroxybutenolides |
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| Authors: | Xiong Xin Ovens Caroline Pilling Adam W Ward John W Dixon Darren J |
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| Institution: | School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK. |
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| Abstract: | The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta-lactol to gamma-substituted beta,gamma-unsaturated alpha-keto esters leading to the direct formation of THP*-protected gamma-hydroxy alpha-keto ester derivatives is described. Subsequent acid-mediated deprotection affords the 3-hydroxybutenolides in high yields. |
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