Chirally and chemically reversible Strecker reaction.

Abstract

In the pursuit of a credible mechanism for the abiotic synthesis of α-amino acids, solid-state asymmetric Strecker/retro-Strecker reactions have been demonstrated. Asymmetric addition of cyanide to enantiomorphic crystals of achiral imines proceeded to produce enantioenriched aminonitriles. Moreover, dehydrocyanation of enantioenriched aminonitriles gave chiral crystals of achiral imines stereoselectively. We found, for the first time to the best of our knowledge, a stereoinversion of the synthetic intermediates imine and aminonitrile in the sequence of reactions including HCN addition and elimination. Thus, the reversible Strecker reaction is expected to be a focus of research on the origin of chirality.