Organocatalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aldehydes

The first organocatalytic asymmetric functionalization of aldehydes with a P-based compound has been successfully developed; the use of a simple chiral secondary amine has enabled the highly chemo- and enantioselective conjugate addition of diphenyl phosphine to α,β-unsaturated aldehydes, providing a direct route to chiral β-phosphine aldehyde intermediates. The synthetic utility of the asymmetric hydrophosphination (AHP) strategy was exemplified in a rapid one-pot (two step) synthesis of highly enantioenriched 1,3-aminophoshines, potentially useful P,N-ligands.