Pd-Catalyzed Enantioselective Allyl-Allyl Cross-Coupling
Ping Zhang, Laura A. Brozek and James P. Morken*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: morkenbc.edu
P. Zhang, L. A. Brozek, J. P. Morken, J. Am. Chem. Soc., 2010, 132, 10686-10688.
DOI: 10.1021/ja105161f (free Supporting Information)
In a Pd-catalyzed cross-coupling of aromatic and aliphatic allylic carbonates and allylB(pin), small-bite-angle ligands favor 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.
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M. J. Ardolino, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 7092-7100.