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The Journal of Organic Chemistry

The Journal of Organic Chemistry

IF: 3.29
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Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine

Published:30 September 2022 DOI: 10.1021/acs.joc.2c01774 PMID: 36179039
Paula Oroz, Claudio D. Navo, Alberto Avenoza, Jesús H. Busto, Francisco Corzana, Gonzalo Jiménez-Osés and Jesús M. Peregrina*, 

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.

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