Access to alpha,alpha-Difluoro-gamma-amino Acids by Nickel-Catalyzed Reductive Aryldifluoroacetylation of N-Vinylacetamide

A nickel-catalyzed reductive aryldifluoroacetylation of N-vinylacetamide with ethyl chloro(difluoro)acetate and aryl iodides is described. This chelating amide carbonyl group-assisted strategy provides rapid access to a variety of protected alpha,alpha-difluoro-gamma-amino acids that might have pote...

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Bibliographic Details
Published inSynlett Vol. 32; no. 15; pp. 1565 - 1569
Main Authors Zhao, Qing-Wei, Yang, Zhi-Fang, Fu, Xia-Ping, Zhang, Xingang
Format Journal Article
LanguageEnglish
German
Published STUTTGART Thieme Medical Publishers 16.09.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
IODIDES
fluoro amino acids
enamides
AMINO-ACIDS
cross-coupling
dicarbofunctionalization
FLUORINE
vinylacetamide
(HETERO)ARYL BROMIDES
DIFLUOROALKYLATION
nickel catalysis
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Summary:A nickel-catalyzed reductive aryldifluoroacetylation of N-vinylacetamide with ethyl chloro(difluoro)acetate and aryl iodides is described. This chelating amide carbonyl group-assisted strategy provides rapid access to a variety of protected alpha,alpha-difluoro-gamma-amino acids that might have potential applications in peptide chemistry and protein engineering. An advantage of this method is its synthetic simplicity, with no preparation of organometallic reagents.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1706553