Direct palladium-catalyzed allylic alkylations of alcohols with enamines: Synthesis of homoallyl ketones

[Display omitted] •Direct catalytic allylic alkylation of enamines with alcohols.•Rapid conversion of α-,β- and γ-substituted alcohols into α-allyl ketones.•A highly regioselective protocol for the synthesis of α- or γ-homoallyl ketones.•A common palladium-based catalyst (Pd(OAc)2), a phosphine liga...

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Bibliographic Details
Published in:Tetrahedron letters 2017-06, Vol.58 (26), p.2525-2529
Main Authors: Bouhalleb, Ghalia, Mhasni, Olfa, Poli, Giovanni, Rezgui, Farhat
Format: Article
Language:English
Subjects:
Allylic alcohol
Allylic substitution
Chemical Sciences
Enamine
Homoallyl ketone
Palladium
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Summary:[Display omitted] •Direct catalytic allylic alkylation of enamines with alcohols.•Rapid conversion of α-,β- and γ-substituted alcohols into α-allyl ketones.•A highly regioselective protocol for the synthesis of α- or γ-homoallyl ketones.•A common palladium-based catalyst (Pd(OAc)2), a phosphine ligand (PPh3), and an inexpensive Lewis acid. An efficient, direct nucleophilic allylic substitution of α-, β- and γ-substituted alcohols with enamines, using the Pd(OAc)2/PPh3 catalyst system and ZnBr2 as a promoter in CH2Cl2 at reflux, is reported. The reaction course was dependent on the steric hindrance at the α- or γ-positions with respect to the functionalized α-carbon, selectively affording in moderate to good yields, α- or γ-homoallyl ketones, the so-called “linear” and “branched” products, respectively.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.05.024