Work

Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors

Year: 2020

Type: article

Abstract: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.0c02665

Authors: Dennis A. Kutateladze, Daniel A. Strassfeld, Eric N. Jacobsen

Institution: Harvard University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G2091016619, Chiral Complexes Designed to Catalyzed Organic Reactions, G5411577050