Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide.
Publication
, Journal Article
Li, H; Widenhoefer, RA
Published in: Tetrahedron
June 2010
Reaction of N-δ-alkenyl-N'-sulfonyl urea 1 with N-iodosuccinimde (NIS; 2 equiv) and a catalytic amount of AgOTf (20 mol %) at room temperature led to intramolecular alkoxyamination to form bicyclic isourea 2a in 95% isolated yield. In comparison, reaction of 1 with NIS and sodium bicarbonate (1 equiv) at room temperature led to isolation of bicyclic imidazolidin-2-one 2b in 91% yield. These NIS-mediated alkoxyamination and diamination protocols were effective for a range of N-δ-alkenyl-N'-sulfonyl ureas to form the corresponding heterobicyclic compounds in good yield with high chemoselectivity and good to excellent diastereoselectivity.
Duke Scholars
Published In
Tetrahedron
DOI
ISSN
0040-4020
Publication Date
June 2010
Volume
66
Issue
26
Start / End Page
4827 / 4831
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Li, H., & Widenhoefer, R. A. (2010). Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide. Tetrahedron, 66(26), 4827–4831. https://doi.org/10.1016/j.tet.2010.03.082
Li, Hao, and Ross A. Widenhoefer. “Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide.” Tetrahedron 66, no. 26 (June 2010): 4827–31. https://doi.org/10.1016/j.tet.2010.03.082.
Li H, Widenhoefer RA. Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide. Tetrahedron. 2010 Jun;66(26):4827–31.
Li, Hao, and Ross A. Widenhoefer. “Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide.” Tetrahedron, vol. 66, no. 26, June 2010, pp. 4827–31. Epmc, doi:10.1016/j.tet.2010.03.082.
Li H, Widenhoefer RA. Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide. Tetrahedron. 2010 Jun;66(26):4827–4831.
Published In
Tetrahedron
DOI
ISSN
0040-4020
Publication Date
June 2010
Volume
66
Issue
26
Start / End Page
4827 / 4831
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry