Stereoselective Synthesis of α,β-Diamino Nitriles from Amino Acids

Manfred T. Reetz; Marcus Hübel; Ralf Jaeger; Renate Schwickardi; Richard Goddard

doi:10.1055/s-1994-25559

Synthesis 1994; 1994(7): 733-738
DOI: 10.1055/s-1994-25559

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Stereoselective Synthesis of α,β-Diamino Nitriles from Amino Acids

Manfred T. Reetz^* , Marcus Hübel, Ralf Jaeger, Renate Schwickardi, Richard Goddard

^*Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany

Abstract

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α-Amino acids 1 are readily converted into the corresponding N, N-dibenzylamino aldehydes 2 which in turn serve as starting materials for enantiomerically pure α- N,N-dibenzylamino aldimines 5, 6 and 7 having benzyl, tosyl and trimethylsilyl groups, respectively, at the aldimine nitrogen atom. All three classes of chiral aldimines undergo stereoselective Lewis acid promoted Me₃SiCN addition reactions with non-chelation controlled formation of the corresponding α,β-diamino nitriles. All of the reaction sequences occur without any racemization.

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