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Visible‐Light‐Enabled Enantioconvergent Synthesis of α‐Amino Acid Derivatives via Synergistic Brønsted Acid/Photoredox Catalysis
Author(s) -
Che Chao,
Li YiNan,
Cheng Xiang,
Lu YiNan,
Wang ChunJiang
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012909
Subject(s) - stereocenter , chemistry , iminium , catalysis , brønsted–lowry acid–base theory , amino acid , organocatalysis , enantioselective synthesis , combinatorial chemistry , glycine , organic chemistry , biochemistry
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.