Gold‐Catalyzed Intermolecular Anti‐Markovnikov Hydroamination of Alkylidenecyclopropanes1. (22nd December 2014)

• Record Type: Journal Article
• Authors: Timmerman, Jacob C.; Robertson, Bradley D.; Widenhoefer, Ross A.
• Is Part Of: Angewandte Chemie. Volume 127:Number 7(2015)
• Page Start: 2279
• Page End: 2282
• Publication Date: 2014-12-22
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201410871
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The cationic gold phosphine complex [{PCy₂(<italic>o</italic>‐biphenyl)}Au(NCMe)]⁺SbF₆⁻ (Cy=cyclohexyl) catalyzes the intermolecular, anti‐Markovnikov hydroamination reaction of monosubstituted and <italic>cis</italic>‐ and <italic>trans</italic>‐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.</p> </abstract>