Intermolecular Hydroamination of Ethylene and 1-Alkenes with Cyclic Ureas Catalyzed by Achiral and Chiral Gold(I) Complexes

TLDR: Reaction of 1-methyl-imidazolidin-2-one with 1-octene catalyzed by a 1:1 mixture of (2b)AuCl and AgSbF(6) in dioxane in 96% yield as a single regioisomer led to isolation and enantioselective intermolecular hydroamination with up to 78% ee.

Abstract: Reaction of 1-methyl-imidazolidin-2-one (1) with 1-octene (10 equiv) catalyzed by a 1:1 mixture of (2b)AuCl [2b = 2-di-tert-butylphosphino-1,1′-binaphthyl] and AgSbF6 in dioxane at 100 °C for 24 h led to isolation of 1-methyl-3-(octan-2-yl)imidazolidin-2-one in 96% yield as a single regioisomer. A range of unactivated 1-alkenes and ethylene underwent gold(I)-catalyzed intermolecular hydroamination at or below 100 °C in excellent yield with high regioselectivity. Reaction of 1-alkenes with substituted imidazolidin-2-ones catalyzed by chiral bis(gold) phosphine complexes led to enantioselective intermolecular hydroamination with up to 78% ee.