Stereospecific transformation of protected P-H group into P-O or P-N group in one-pot reaction.

State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

The Journal of organic chemistry 2012 Dec 7

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A general and efficient procedure for converting 1,1-diethoxyalkylphosphinates into phosphonates or phosphonamides is described by the application of bromine with moderate to high yields and good purity in a one-pot reaction. H-Phosphinate reacts stereospecifically with bromine and subsequently couples with nucleophile to form the corresponding optically active R(1)P(O)(OEt)X with retention of configuration at the phosphorus center. For α-amino-H-phosphinates, the transformation could be realized without the protection of the amino group.

Citation

Qiuli Yao, Chengye Yuan. Stereospecific transformation of protected P-H group into P-O or P-N group in one-pot reaction. The Journal of organic chemistry. 2012 Dec 7;77(23):10985-90