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Metal-Free C–H Functionalization of Allenamides: An Access to Branched Allylic Esters
Author(s) -
Guoli Luo,
Yongchun Liu,
Na Ding,
Xiaoxiao Li,
Zhigang Zhao
Publication year - 2019
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.9b02712
Subject(s) - allylic rearrangement , regioselectivity , surface modification , substrate (aquarium) , chemistry , combinatorial chemistry , amino acid , organic chemistry , catalysis , biochemistry , biology , ecology
A regioselective acyloxylation with carboxylic acids at the proximal carbon of allenamides by an N -iodosuccinimide-mediated C-H functionalization is reported. The reaction proceeds rapidly, is scalable to a gram scale, and displays a broad substrate scope, providing an efficient and practical protocol for the synthesis of branched allylic esters. Notably, protected amino acids were tolerated under the reaction conditions and afforded allylic amino acid esters in moderate yields.

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