Tetrahedron

[HP (HNCH 2 CH 2) 3 N] NO 3: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions

BM Fetterly, NK Jana, JG Verkade

Index: Fetterly, Brandon M.; Jana, Nirmal K.; Verkade, John G. Tetrahedron, 2006 , vol. 62, # 2-3 p. 440 - 456

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Citation Number: 74

Abstract

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.