Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes.
Published
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