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.
Wang
Gang
G
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, China.
Shen
Ruwei
R
Xu
Qing
Q
Goto
Midori
M
Zhao
Yufen
Y
Han
Li-Biao
LB
D000438:Alcohols / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D008722:Methods; D009904:Optical Rotation; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D010087:Oxides / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D010757:Phosphorous Acids / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000588:Amines; D009943:Organophosphorus Compounds; D010087:Oxides; D010720:Phosphines; D010757:Phosphorous Acids; C044646:phosphine; C043639:metaphosphoric acid