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Synfacts 2006(8): 0805-0805  
DOI: 10.1055/s-2006-942011
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Aerobic Oxidation ofα-Hydroxyphosphonates

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
V. D. Pawar, S. Bettigeri, S.-S. Weng, J.-Q. Kao, C.-T. Chen*
National Taiwan Normal University, Taipei, Taiwan
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

This is an excellent report on the synthesis of enantioenriched α-hydroxyphosphonates through kinetic resolution. The use of various substitutents on the N-salicylidene led to the finding that the dibromo analogue (shown in 1) gave the best ee values and k rel. A large number of α-aryl-substituted α-hydroxyphosphonates were shown to be compatible giving >96% ee (at 49-51% conversion) in most cases with >99% k rel in almost all cases. Saturated α-alkyl-substituted α-hydroxyphosphonates were not compatible, but the use of the unsaturated crotonyl-substituted substrate gave the product in 96% ee at 49% conversion.