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Synfacts 2007(10): 1032-1032  
DOI: 10.1055/s-2007-968971
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Enantioselective Synthesis of γ-Butyrolactones

Contributor(s): Victor Snieckus, Jignesh J. Patel
J. Song, Q. Shen*, F. Xu, X. Lu*
Suzhou University and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
07 November 2007 (online)

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Significance

Reported is a cationic Pd(II)-catalyzed reaction of alkynoyl ketones to α-alkylidine-β-hydroxy-γ-lactones in good to excellent yields. The reaction consists of an intermolecular carbopalladation of an alkynoate by arylboronic acids and subsequent intramolecular addition of the resulting vinylpalladium species to a carbonyl to form the α-alkylidene-β-hydroxy-γ-lactone products. The catalyst system Pd(OAc)2/dppp performed sluggishly in the reaction. The Pd(O2CCF3)2-(S,S)-BDPP catalyst-ligand system performed best in the asymmetric version of this cyclization.