Diastereoselective and Enantioselective Synthesis of Tertiary α-Hydroxy Phosphonates through Hydrogen-Bond Catalysis


  • This work was supported by the National Institutes of Health (USA). We thank Kyowa Hakko Co., Ltd. (Japan) for a sabbatical fellowship to K.H., and Prof. Dr. Chong Zheng (Northern Illinois University) for the crystal structure of 15 g.


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Hydrogen-bond activation by a diol promotes enantioselective Mukaiyama aldol reactions of acyl phosphonates. This mild and general method gives α-hydroxy phosphonate products having two chiral centers, one tertiary and one quaternary, formed with high diastereo- and enantioselectivity.