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The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5-exo cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90:10 to 95:5 e.r.. These processes are rare examples of reactions that proceed via enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.
- BCS and TECS CDTs
Race, N., Faulkner, A., Fumagalli, G., Yamauchi, T., Scott, J. S., Marie, R-L., Sparkes, H., & Bower, J. (2017). Enantioselective Narasaka-Heck Cyclizations: Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters. Chemical Science, 8(3), 1981-1985. https://doi.org/10.1039/C6SC04466B