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Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine.

ABSTRACT: Chemo- and diastereoselective 1,4-conjugate additions of anionic and radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, radical carbon photolysis by a catalytic photoredox process using a simple method with a metal-free photocatalyst provides exceptional yields and selectivities at room temperature. Moreover, these 1,4-conjugate additions offer an excellent starting point for synthesizing enantiomerically pure carbon-β-substituted unnatural α-amino acids (UAAs), which could have a high potential for applications in chemical biology.

SUBMITTER: Oroz P

PROVIDER: S-EPMC9639051 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine.

Oroz Paula P Navo Claudio D CD Avenoza Alberto A Busto Jesús H JH Corzana Francisco F Jiménez-Osés Gonzalo G Peregrina Jesús M JM

The Journal of organic chemistry 20220930 21

Chemo- and diastereoselective 1,4-conjugate additions of anionic and radical <i>C</i>-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, radical carbon photolysis by a catalytic photoredox process using a simple method with a metal-free photocatalyst provides exceptional yields and selectivities at room temperature. Moreover, these 1,4-conjugate additions offer an excellent starting point for synthesizing enantiomerically pure carbon-β-substituted unn ...[more]

PMID: 36179039

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