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Palladium‐Catalyzed Decarboxylative γ‐Arylation for the Synthesis of Tetrasubstituted Chiral Allenes
Author(s) -
Scheipers Ina,
MückLichtenfeld Christian,
Studer Armido
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201901848
Subject(s) - palladium , catalysis , decarboxylation , aryl , chemistry , chirality (physics) , allene , coupling (piping) , organic chemistry , combinatorial chemistry , materials science , physics , chiral symmetry , alkyl , nambu–jona lasinio model , metallurgy , quark , quantum mechanics
Abstract An enantiospecific palladium‐catalyzed decarboxylative coupling of acyclic β,γ‐alkynoic acids with various aryl iodides to chiral tetrasubstituted allenes is described. The coupling reaction comprises a decarboxylative γ‐palladation of α,α‐disubstituted carboxylic acids to provide the tetrasubstituted allenes with complete point‐to‐axial chirality transfer in excellent yields.