Palladium‐Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β‐ketoesters: An Unusual Counterion Effect | Zendy

Trost Barry M. | Zendy; Schäffner Benjamin | Zendy; Osipov Maksim | Zendy; Wilton Donna A. A. | Zendy

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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.

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