Organocatalytic asymmetric hydrophosphination of α,β-unsaturated aldehydes

Abstract

Getting round the (periodic) table: A highly chemo- and enantioselective conjugate addition of diphenylphosphine to α,β-unsaturated aldehydes in the presence of a chiral secondary amine C provides a direct route to chiral β-phosphino aldehyde intermediates (see scheme, TMS = trimethylsilyl). The synthetic utility of the strategy was exemplified in a rapid one-pot (two-step) synthesis of highly enantioenriched 3-amino-phosphines. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.