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Palladium‐Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β‐ketoesters: An Unusual Counterion Effect
Author(s) -
Trost Barry M.,
Schäffner Benjamin,
Osipov Maksim,
Wilton Donna A. A.
Publication year - 2011
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.201007803
Subject(s) - palladium , tetrahydrofuran , chemistry , catalysis , organic chemistry , tsuji–trost reaction , alkylation , computer science , solvent
Buy one, get one free : Both enantiomers of tetralone and indanone derivatives are available in a one‐pot procedure from allyl chloroformate and their β‐ketoesters by using the same catalyst system (see scheme; dba=dibenzylideneacetone, 1,2‐DCE=1,2‐dichloroethane, THF=tetrahydrofuran). The details of this remarkable effect were investigated by performing scavenging experiments and a variety of substrates were successfully used in the procedure.