Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes.

Journal Article (Journal Article)

The cationic gold phosphine complex [{PCy2 (o-biphenyl)}Au(NCMe)](+) SbF6 (-) (Cy=cyclohexyl) catalyzes the intermolecular, anti-Markovnikov hydroamination reaction of monosubstituted and cis- and trans-disubstituted alkylidenecyclopropanes (ACPs) with imidazolidin-2-ones and other nucleophiles. This reaction forms 1-cyclopropyl alkylamine derivatives in high yield and with high regio- and diastereoselectivity. NMR spectroscopic analysis of gold π-ACP complexes and control experiments point to the sp hybridization of the ACP internal alkene carbon atom as controlling the regiochemistry of the ACP hydroamination reaction.

Full Text

Duke Authors

Cited Authors

  • Timmerman, JC; Robertson, BD; Widenhoefer, RA

Published Date

  • February 2015

Published In

Volume / Issue

  • 54 / 7

Start / End Page

  • 2251 - 2254

PubMed ID

  • 25533892

Pubmed Central ID

  • 25533892

Electronic International Standard Serial Number (EISSN)

  • 1521-3773

International Standard Serial Number (ISSN)

  • 1433-7851

Digital Object Identifier (DOI)

  • 10.1002/anie.201410871

Language

  • eng