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Au(I)-Catalyzed Oxidative Functionalization of Yndiamides
Author(s) -
Zixuan Tong,
Olivia L. Garry,
Philip CameronSmith,
Yubo Jiang,
Steven J. Mansfield,
Edward A. Anderson
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01625
Subject(s) - chemistry , steric effects , regioselectivity , nucleophile , surface modification , catalysis , oxidative phosphorylation , combinatorial chemistry , functional group , nitrogen atom , nitrogen , stereochemistry , group (periodic table) , organic chemistry , biochemistry , polymer
Yndiamides, underexplored cousins of ynamides, offer rich synthetic potential as doubly nitrogenated two carbon building blocks. Here we report a gold-catalyzed oxidative functionalization of yndiamides to access unnatural amino acid derivatives, using a wide range of nucleophiles as a source of the amino acid side chain. The transformation proceeds under mild conditions, is highly functional group tolerant, and displays excellent regioselectivity through subtle steric differentiation of the yndiamide nitrogen atom substituents.

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