Deracemization by coupling electrochemically assisted racemization and asymmetric crystallization

TL;DR

A new method combines electrochemistry and crystallization to efficiently convert mixtures of amino acid derivatives into pure enantiomers.

Contribution

A one-pot, two-step deracemization method using electrochemical racemization and chiral amplification is introduced.

Findings

Full enantioselective conversion (e.e. > 99%) was achieved for amino acid derivatives and paclobutrazol precursor.

The method uses in situ electrochemical base generation and crystallization-induced chiral amplification.

The approach enables deracemization in a single pot with two steps.

Abstract

Amino acid derivatives of tert-leucine and phenyl glycine along with plant growth retardant and the precursor of fungicide paclobutrazol are deracemized by combining in situ electrochemical base generation to induce racemization and crystallization-induced chiral amplification in a one-pot, two-step deracemization procedure. Full enantioselective conversion (e.e. > 99%) of a mixture of enantiomers towards the desired handedness is achieved.

Amino acid derivatives and paclobutrazol precursor are deracemized by combining in situ electrochemical base generation, inducing racemization and crystallization-driven chiral amplification in a one-pot, two-step approach.

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