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.
Duke Scholars
Altmetric Attention Stats
Dimensions Citation Stats
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
Citation
APA
Chicago
ICMJE
MLA
NLM
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.
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