Tetrahedron letters

Synthesis and stereoselective reductions of chiral β-iminosulfoxides

JLG Ruano, A Lorente, JH Rodríguez

Index: Garcia Ruano; Lorente; Rodriguez Tetrahedron Letters, 1992 ,  vol. 33,  # 38  p. 5637 - 5640

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Citation Number: 19

Abstract

Abstract Reaction of chiral non racemic β-ketosulfoxides with amines or condensation of the imine enolates with (−)-methyl sulfinate yield optically pure β-iminosulfoxides. The second method requires the presence of an excess of MgBr 2 in order to avoid epimerization at sulfur. The highly diastereoselective reduction of these substrates can be successfully achieved only with DIBAL/ZnBr 2 (de 97%). Hydrogenolysis of the C S bond on the ...