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

J Am Chem Soc. 2017 Mar 15;139(10):3631-3634. doi: 10.1021/jacs.7b00437. Epub 2017 Mar 6.

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.

Publication types

  • Research Support, Non-U.S. Gov't