Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides
Naoyuki Suzuki, Julie L. Hofstra, Kelsey E. Poremba and Sarah E. Reisman*
*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: reismancaltech.edu
N. Suzuki, J. L. Hofstra, K. E. Poremba, S. E. Reisman, Org. Lett., 2017, 19, 2150-2153.
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An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with excellent enantioselectivity.
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A. H. Cherney, S. E. Reisman, J. Am. Chem. Soc., 2014, 136, 14365-14366.