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

• Published in: Journal of organic chemistry Vol. 75; no. 11; pp. 3890 - 3892
• Main Authors: Wang, Gang, Shen, Ruwei, Xu, Qing, Goto, Midori, Zhao, Yufen, Han, Li-Biao
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.06.2010; Amer Chemical Soc
• Subjects: Alcohols - chemistry; Amines - chemistry; Chemistry; Chemistry, Organic; Exact sciences and technology; Methods; Optical Rotation; Organic chemistry; Organometalloidal and organometallic compounds; Organophosphorus Compounds - chemical synthesis; Oxides - chemistry; P derivatives; Phosphines - chemistry; Phosphorous Acids - chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; INHIBITORS; ABSOLUTE-CONFIGURATION; BOND; STEREOCHEMISTRY; Configuration inversion; Amine; Optical activity; Organic phosphinate; Alcohol; Organic phosphorus compounds; Stereospecificity; Chiral compound; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo100473s

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.