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

Published

Journal Article

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.

Full Text

Duke Authors

Cited Authors

  • Zhang, Z; Lee, SD; Widenhoefer, RA

Published Date

  • April 2009

Published In

Volume / Issue

  • 131 / 15

Start / End Page

  • 5372 - 5373

PubMed ID

  • 19326908

Pubmed Central ID

  • 19326908

Electronic International Standard Serial Number (EISSN)

  • 1520-5126

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja9001162

Language

  • eng