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Chiral Phosphaalkene-Oxazoline Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation.

TitleChiral Phosphaalkene-Oxazoline Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation.
Publication TypeJournal Article
Year of Publication2010
AuthorsDugal-Tessier, J, Dake, GR, Gates, DP
JournalOrganic Letters
Volume12
Pagination4667 - 4669
Date Published2010///
ISBN Number1523-7060
Keywordsdiphenylallyl malonate prepn phosphaalkene oxazoline palladium catalyzed allylic alkylation, diphenylpropenyl acetate malonate reactant stereoselective allylic alkylation palladium catalyst, enantioselective palladium catalyzed allylic alkylation phosphaalkene oxazoline ligand
Abstract

Enantioselective catalysis in moderate to excellent yields and ee’s has been accomplished using a phosphaalkene-based ligand system. Specifically, the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate using a chiral P(sp2),N(sp2) ligand proceeds with a variety of malonate nucleophiles to give the desired malonates, e.g. I, in 73-95% yield (79-92% ee). [on SciFinder(R)]