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Synthesis of Enantioenriched ?-Deuterated ?-Amino Acids Enabled by an Organophotocatalytic Radical Approach.

ABSTRACT: A mild, versatile organophotoredox protocol has been developed for the preparation of diverse, enantioenriched ?-deuterated ?-amino acids. Distinct from the well-established two-electron transformations, this radical-based strategy offers the unrivaled capacity of the convergent unification of readily accessible feedstock carboxylic acids and a chiral methyleneoxazolidinone fragment and the simultaneous highly diastereo-, chemo-, and regioselective incorporation of deuterium. Furthermore, the approach has addressed the long-standing challenge of the installation of sterically demanding side chains into ?-amino acids.

SUBMITTER: Ji P

PROVIDER: S-EPMC7936574 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Synthesis of Enantioenriched α-Deuterated α-Amino Acids Enabled by an Organophotocatalytic Radical Approach.

Ji Peng P Zhang Yueteng Y Dong Yue Y Huang He H Wei Yongyi Y Wang Wei W

Organic letters 20200211 4

A mild, versatile organophotoredox protocol has been developed for the preparation of diverse, enantioenriched α-deuterated α-amino acids. Distinct from the well-established two-electron transformations, this radical-based strategy offers the unrivaled capacity of the convergent unification of readily accessible feedstock carboxylic acids and a chiral methyleneoxazolidinone fragment and the simultaneous highly diastereo-, chemo-, and regioselective incorporation of deuterium. Furthermore, the ap ...[more]

PMID: 32045253

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