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Enantioselective Terminal Addition to Allenes by Dual Chiral Primary Amine/Palladium Catalysis.

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We herein describe a synergistic chiral primary amine/achiral palladium catalyzed enantioselective terminal addition to allenes with α-branched β-ketocarbonyls and aldehydes. The reactions afford allylic adducts bearing acyclic all-carbon quaternary centers… Click to show full abstract

We herein describe a synergistic chiral primary amine/achiral palladium catalyzed enantioselective terminal addition to allenes with α-branched β-ketocarbonyls and aldehydes. The reactions afford allylic adducts bearing acyclic all-carbon quaternary centers with high regio- and enantioselectivity. A wide range of allenes including those aliphatic or 1,1'-disubstituted could be employed, thus expanding the scope of typical asymmetric allylic alkylation reactions.

Keywords: enantioselective terminal; terminal addition; palladium; addition allenes; primary amine; chiral primary

Journal Title: Journal of the American Chemical Society
Year Published: 2017

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