Asymmetric synthesis of phosphonotrifluoroalanine derivatives via proline-catalyzed direct enantioselective CC bond formation reactions of NH trifluoroacetimidoyl phosphonate
2014
Abstract Based on enantioselective proline-catalyzed reactions between NH-iminotrifluoroethylphosphonate and acetone, an effective synthetic approach to both enantiomers of α-amino-α-trifluoromethyl-γ-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 3 H -pyrrolizines, incorporating pharmacophoric optically active fragments of phosphonotrifluoroalanine.
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