Asymmetric synthesis of phosphonotrifluoroalanine derivatives via proline-catalyzed direct enantioselective C-C bond formation reactions of N-H trifluoroacetimidoyl phosphonate

作者：Rassukana Yuliya V; Yelenich Ivanna P; Vlasenko Yurii G; Onys'ko Petro P^*

来源：Tetrahedron: Asymmetry , 2014, 25(16-17): 1234-1238.

DOI：10.1016/j.tetasy.2014.07.007

Based on enantioselective proline-catalyzed reactions between NH-iminotrifluoroethylphosphonate and acetone, an effective synthetic approach to both enantiomers of alpha-amino-alpha-trifluoromethyl-gamma-oxobutylphosphonate was developed. The synthetic potential of these novel chiral synthons was illustrated by their cyclocondensation reactions with 4-chlorophenylisocyanate or 2,5-dimethoxytetrahydrofuran to afford the first representatives of phosphorylated 3,4-dihydropyrimidin-2-ones or 3H-pyrrolizines, incorporating pharmacophoric optically active fragments of phosphonotrifluoroalanine.

• 出版日期2014-9-15