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Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes.

Publication ,  Journal Article
Timmerman, JC; Robertson, BD; Widenhoefer, RA
Published in: Angewandte Chemie (International ed. in English)
February 2015

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.

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Published In

Angewandte Chemie (International ed. in English)

DOI

EISSN

1521-3773

ISSN

1433-7851

Publication Date

February 2015

Volume

54

Issue

7

Start / End Page

2251 / 2254

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

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Timmerman, J. C., Robertson, B. D., & Widenhoefer, R. A. (2015). Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes. Angewandte Chemie (International Ed. in English), 54(7), 2251–2254. https://doi.org/10.1002/anie.201410871
Timmerman, Jacob C., Bradley D. Robertson, and Ross A. Widenhoefer. “Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes.Angewandte Chemie (International Ed. in English) 54, no. 7 (February 2015): 2251–54. https://doi.org/10.1002/anie.201410871.
Timmerman JC, Robertson BD, Widenhoefer RA. Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes. Angewandte Chemie (International ed in English). 2015 Feb;54(7):2251–4.
Timmerman, Jacob C., et al. “Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes.Angewandte Chemie (International Ed. in English), vol. 54, no. 7, Feb. 2015, pp. 2251–54. Epmc, doi:10.1002/anie.201410871.
Timmerman JC, Robertson BD, Widenhoefer RA. Gold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes. Angewandte Chemie (International ed in English). 2015 Feb;54(7):2251–2254.
Journal cover image

Published In

Angewandte Chemie (International ed. in English)

DOI

EISSN

1521-3773

ISSN

1433-7851

Publication Date

February 2015

Volume

54

Issue

7

Start / End Page

2251 / 2254

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences