Issue 17, 2023

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.

Graphical abstract: Chirally and chemically reversible Strecker reaction

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Jan 2023
Accepted
28 Mar 2023
First published
28 Mar 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 4480-4484

Chirally and chemically reversible Strecker reaction

Y. Machida, Y. Tanaka, Y. Masuda, A. Kimura and T. Kawasaki, Chem. Sci., 2023, 14, 4480 DOI: 10.1039/D3SC00359K

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