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. 2009 Apr 22;131(15):5372-3.
doi: 10.1021/ja9001162.

Intermolecular hydroamination of ethylene and 1-alkenes with cyclic ureas catalyzed by achiral and chiral gold(I) complexes

Zhibin Zhang  1 , Seong Du Lee, Ross A Widenhoefer
Affiliations

Intermolecular hydroamination of ethylene and 1-alkenes with cyclic ureas catalyzed by achiral and chiral gold(I) complexes

Zhibin Zhang et al. J Am Chem Soc. .

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 AgSbF(6) in dioxane at 100 degrees 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 degrees 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.

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