Diastereoselective Synthesis of Adjacent P,C-Stereogenic ss-N-Glycosidic Linked alpha-Aminophosphinates

作者：Liu, Shuang; Li, Yuming; Yin, Zhiyu; Yu, Qiuli; Miao, Zhiwei^*

来源：Journal of Organic Chemistry, 2017, 82(5): 2481-2488.

DOI：10.1021/acs.joc.6b02877

• BAYLIS-HILLMAN CARBONATES
• CATALYTIC ENANTIOSELECTIVE HYDROPHOSPHONYLATION
• PURE H-PHOSPHINATE
• ASYMMETRIC-SYNTHESIS
• AMINO PHOSPHONATES
• ALPHA,BETA-UNSATURATED ALDEHYDES
• PHOSPHORUS-COMPOUNDS
• AL(SALALEN) COMPLEX
• OXIDES
• ACIDS

The diastereoselective formation Of adjacent P,C-stereogenic)ss N-glytogidic linked alpha-aminophosphinates is developed in high yields via a phospha-Mannich reaction. The reaction was performed by employing (R-p),-O-(-)-thenthyl H-phenylphosphinate and 0-pivaloylated N-galactosylimine for double stereoclifferentiation and BF3 center dot Et2O as a promoter in THF-O-Pivaloylated N-galactosylphenyl imine 2 and (R-p)-O-(-)-menthyl H-phenylphovhinate 1 were converted to N-galactosyl alpha-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 alpha-aminophosphinates.

• 出版日期2017-3-3
• 单位南开大学