Congested C-C Bonds by Pd-Catalyzed Enantioselective Allyl-Allyl Cross-Coupling, a Mechanism-Guided Solution
Michael J. Ardolino and James P. Morken*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: morkenbc.edu
M. J. Ardolino, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 7092-7100.
DOI: 10.1021/ja502280w (free Supporting Information)
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Optimized reaction conditions expand the scope of Pd-catalyzed allyl-allyl couplings to allow the generation of 1,5-dienes with tertiary centers adjacent to quaternary centers as well as a unique set of cyclic structures. Using a chiral bidentate diphosphine ligand, the asymmetric cross-coupling of allylboron reagents and allylic electrophiles establishes 1,5-dienes with adjacent stereocenters in high regio- and stereoselectivity.
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P. Zhang, L. A. Brozek, J. P. Morken, J. Am. Chem. Soc., 2010, 132, 10686-10688.