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

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 ex...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 21; pp. 14308 - 14318
Main Authors Oroz, Paula, Navo, Claudio D., Avenoza, Alberto, Busto, Jesús H., Corzana, Francisco, Jiménez-Osés, Gonzalo, Peregrina, Jesús M.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2022
Amer Chemical Soc
Subjects
Amino Acids
Carbon
Catalysis
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Stereoisomerism
GLYCINE
ACTIVATION
ASYMMETRIC-SYNTHESIS
MICHAEL ADDITIONS
NI(II) COMPLEXES
PEPTIDE
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:Marie Curie Actions (MSCA)
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01774