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Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd‐Catalyzed Decarboxylation of Enol Carbonate and β‐Ketoester Substrates
Author(s) -
Trost Barry M.,
Bream Robert N.,
Xu Jiayi
Publication year - 2006
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.200504421
Subject(s) - decarboxylation , enol , chemistry , allylic rearrangement , tsuji–trost reaction , catalysis , alkylation , palladium , carbonate , combinatorial chemistry , organic chemistry
Excellent yields and enantioselectivities were achieved for the palladium‐catalyzed asymmetric allylic alkylation of vinylogous thioesters. The close‐to‐neutral reaction conditions ensure that this reaction can tolerate a wide range of functionalities. Furthermore, this approach provides a convenient protocol for the synthesis of synthetically important α,α‐ and γ,γ‐disubstituted cycloalkenones.