Visible-Light-Enabled Enantioconvergent Synthesis of α-Amino Acid Derivatives via Synergistic Brønsted Acid/Photoredox Catalysis.
Brønsted acid catalysis
photoredox catalysis
radical addition
synergistic catalysis
unnatural α-amino acids
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
23 02 2021
23 02 2021
Historique:
received:
23
09
2020
revised:
10
11
2020
pubmed:
22
11
2020
medline:
22
11
2020
entrez:
21
11
2020
Statut:
ppublish
Résumé
An unprecedented radical cross-coupling reaction was achieved between glycine esters and racemic α-bromoketones catalyzed by synergistic Brønsted acid/photoredox catalysis, thus serving as an efficient platform for the synthesis of highly valuable enantioenriched unnatural α-amino acid derivatives. This dual catalysis provides a powerful capability to control the reactive radical intermediate and iminium ion, thereby enabling enantioconvergent bond-formation in a highly stereochemical manner. An array of valuable enantioenriched unnatural α-amino acid derivatives bearing two contiguous stereogenic centers are readily accessible with high diastereoselectivity and excellent enantioselectivity, which include α-amino acids with a unique β-fluorinated quaternary stereocenter or its β-all-carbon counterpart. A strong chiral amplification effect was observed in this dual catalytic system.
Identifiants
pubmed: 33219607
doi: 10.1002/anie.202012909
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
4698-4704Informations de copyright
© 2020 Wiley-VCH GmbH.
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