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Enantioselective Palladium-Catalyzed Domino Carbonylative Heck Esterification of o -Iodoalkenylbenzenes with Arylboronic Acids.

Authors :
Zhang YD
Chen M
Li Y
Liu BW
Ren ZH
Guan ZH
Source :
Organic letters [Org Lett] 2023 Nov 17; Vol. 25 (45), pp. 8110-8115. Date of Electronic Publication: 2023 Nov 03.
Publication Year :
2023

Abstract

The current investigation presents an innovative palladium-catalyzed asymmetric carbonylative Heck esterification method. This approach facilitates the efficient synthesis of various chiral γ-ketoacid esters by utilizing o -alkenyliodobenzenes and arylboronic acids as primary substrates. This reaction achieves the creation of three carbon-carbon bonds, two carbon-oxygen bonds, and the establishment of a quaternary carbon center within a single step. The α-chiral γ-ketoacid esters were obtained in yields ranging from good to high yields, displaying enantiomeric excesses (ee's) levels up to 92% under mild reaction conditions.

Details

Language :
English
ISSN :
1523-7052
Volume :
25
Issue :
45
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
37921830
Full Text :
https://doi.org/10.1021/acs.orglett.3c03189