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

Autor:	Kutateladze DA; Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States., Strassfeld DA; Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States., Jacobsen EN; Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2020 Apr 15; Vol. 142 (15), pp. 6951-6956. Date of Electronic Publication: 2020 Apr 03.
DOI:	10.1021/jacs.0c02665
Abstrakt:	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.
Databáze:	MEDLINE
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