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Pd-catalyzed enantioselective allyl-allyl cross-coupling.

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.

SUBMITTER: Zhang P

PROVIDER: S-EPMC2925184 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Pd-catalyzed enantioselective allyl-allyl cross-coupling.

Zhang Ping P Brozek Laura A LA Morken James P JP

Journal of the American Chemical Society 20100801 31

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 car ...[more]

PMID: 20681700

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