Stereospecific coupling of H-phosphinates and secondary phosphine oxides with amines and alcohols: a general method for the preparation of optically active organophosphorus acid derivatives.

The reaction of H-phosphinates and secondary phosphine oxides with amines and alcohols proceeds highly stereospecifically to give the corresponding coupling products with inversion of configuration at the phosphorus center under the Atherton-Todd reaction conditions. This finding leads to the establishment of a general and efficient method for the synthesis of a variety of optically active organophosphorus acid derivatives from the easily available chiral H-phosphinates and secondary phosphine oxides.

Citation

Gang Wang, Ruwei Shen, Qing Xu, Midori Goto, Yufen Zhao, Li-Biao Han. Stereospecific coupling of H-phosphinates and secondary phosphine oxides with amines and alcohols: a general method for the preparation of optically active organophosphorus acid derivatives. The Journal of organic chemistry. 2010 Jun 4;75(11):3890-2

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PMID: 20443613

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