Diastereoselective Synthesis of Adjacent P,C-Stereogenic β- N -Glycosidic Linked α-Aminophosphinates

作者：Shuang Liu, Yuming Li, Zhiyu Yin, Qiuli Yu, Zhiwei Miao · 发表于：The Journal of Organic Chemistry · 年份：2017 · DOI：10.1021/acs.joc.6b02877 · 被引用次数：8 · 研究领域：Organophosphorus compounds synthesis、Carbohydrate Chemistry and Synthesis、Asymmetric Hydrogenation and Catalysis

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 ( R p )- O -(−)-menthyl H -phenylphosphinate and O -pivaloylated N -galactosylimine for double stereodifferentiation and BF 3 ·Et 2 O as a promoter in THF. O -Pivaloylated N -galactosylphenyl imine 2 and ( R p )- 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.