Synfacts 2009(1): 0053-0053  
DOI: 10.1055/s-0028-1087439
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective, Catalytic Pd(II)-Based Allylic Alkylation

Contributor(s): Hisashi Yamamoto, Marina Naodovic
A. J. Young, M. C. White*
University of Illinois, Urbana, USA
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Publikationsverlauf

Publikationsdatum:
18. Dezember 2008 (online)

Significance

The methodology described in this report is one of the first direct catalytic allylic C-H alkylation reactions. White and Young have introduced a novel set of reaction conditions, allowing the reaction to proceed in a truly catalytic fashion. The use of DMSO as an π-acceptor ligand facilitates nucleophilic functionalization of the π-allylPd intermediate, while the combination of sterically bulkier 2,6-dimethylbenzoquinone (DMBQ) and AcOH serves as an oxidant, activating agent of π-allylPd species toward reductive elimination and as a source of catalytic base.