172823-06-2Relevant articles and documents
Diastereoselective Synthesis of Adjacent P,C-Stereogenic β-N-Glycosidic Linked α-Aminophosphinates
Liu, Shuang,Li, Yuming,Yin, Zhiyu,Yu, Qiuli,Miao, Zhiwei
, p. 2481 - 2488 (2017/03/14)
The diastereoselective formation of adjacent P,C-stereogenic β-N-glycosidic linked α-aminophosphinates is developed in high yields via a phospha-Mannich reaction. The reaction was performed by employing (Rp)-O-(?)-menthyl H-phenylphosphinate and O-pivaloylated N-galactosylimine for double stereodifferentiation and BF3·Et2O as a promoter in THF. O-Pivaloylated N-galactosylphenyl imine 2 and (Rp)-O-(?)-menthyl H-phenylphosphinate 1 were converted to N-galactosyl α-aminoalkylphosphinate 3 with ratios of diastereomers up to 20:1. The synthetic method of the conversion provides a rapid access to adjacent P,C-stereogenic chiral α-aminophosphinates.
Stereospecific nucleophilic substitution of optically pure H-phosphinates: A general way for the preparation of chiral P-stereogenic phosphine oxides
Xu, Qing,Zhao, Chang-Qiu,Han, Li-Biao
supporting information; experimental part, p. 12648 - 12655 (2009/05/09)
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 reactio
