Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors,Journal of the American Chemical Society

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Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-03-28 , DOI: 10.1021/jacs.0c02665
Dennis A Kutateladze ₁ , Daniel A Strassfeld ₁ , Eric N Jacobsen ₁

Affiliation

Chiral urea derivatives are shown to catalyze enantioselective tail-to-head cyclization reactions of neryl chloride analogues. Experimental data are consistent with a mechanism in which π-participation by the nucleophilic olefin facilitates chloride ionization and thereby circumvents simple elimination pathways. Kinetic and computational studies support a cooperative mode of catalysis wherein two molecules of the urea catalyst engage the substrate and induce enantioselectivity through selective transition state stabilization.

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