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. 2010 Aug 11;132(31):10686-8.
doi: 10.1021/ja105161f.

Pd-catalyzed enantioselective allyl-allyl cross-coupling

Ping Zhang  1 , Laura A Brozek, James P Morken
Affiliations

Pd-catalyzed enantioselective allyl-allyl cross-coupling

Ping Zhang et al. J Am Chem Soc. .

Abstract

The Pd-catalyzed cross-coupling of allylic carbonates and allylB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of regioselection is consistent with a reaction that operates by a 3,3' reductive elimination reaction. In the presence of appropriate chiral ligands, this reaction is rendered enantioselective and applies to both aromatic and aliphatic allylic carbonates.

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