[HP(HNCH2CH2)3N]NO3: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions

In the presence of a catalytic amount of an azaphosphatrane nitrate salt, amines and thiols react readily with Michael acceptors. The salt is also an efficient promoter for the one pot synthesis of α-amino and α-amidonitriles. By anchoring the salt to Merrifield Resin, a reusable heterogeneous catalyst is obtained for these reactions. Evidence is presented for catalysis being attributable solely to the NO3− ion.