Stereospecific nucleophilic substitution of optically pure H-phosphinates: a general way for the preparation of chiral P-stereogenic phosphine oxides

Q Xu, CQ Zhao, LB Han

Index: Xu, Qing; Zhao, Chang-Qiu; Han, Li-Biao Journal of the American Chemical Society, 2008 , vol. 130, # 38 p. 12648 - 12655

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Citation Number: 92

Abstract

Contrary to the generally held view, it is found that the rapid epimerization of (−)-menthyl (RP)-phenylphosphinate under basic conditions is not due to the so far believed inherent stereolability of its corresponding anion but due to a reaction of the hydrogen phosphinate ester with a metal alkoxide. This finding successfully leads to a discovery that, by adding an H-phosphinate to organolithiums or Grignard reagents at a low temperature, the ...