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Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect

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  • We thank the US National Science Foundation for their generous support of our program. B.S. is grateful to the Alexander von Humboldt Foundation for a Feodor Lynen-Fellowship. M.O. is a John Stauffer Memorial Fellow. D.A.A.W. is grateful for a Lindemann postdoctoral scholarship from the English-Speaking Union.

Abstract

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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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