Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides |
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| Authors: | Travis J DeLano Sara E Dibrell Caitlin R Lacker Adam R Pancoast Kelsey E Poremba Leah Cleary Matthew S Sigman Sarah E Reisman |
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| Institution: | The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena California 91125 USA.; Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City Utah 84112 USA |
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| Abstract: | An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity.A Ni-catalyzed enantioselective reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. A MLR model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity. |
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