Diastereoselective Synthesis of Adjacent P,C-Stereogenic β-N-Glycosidic Linked α-Aminophosphinates.
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.
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Weijin Road 94, Tianjin 300071, China.
Shuang
S
Liu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Weijin Road 94, Tianjin 300071, China.
Yuming
Y
Li
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Weijin Road 94, Tianjin 300071, China.
Zhiyu
Z
Yin
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Weijin Road 94, Tianjin 300071, China.
Qiuli
Q
Yu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Weijin Road 94, Tianjin 300071, China.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, China.
Zhiwei
0000-0002-8488-8670
Z
Miao