Regio- and diastereoselective ring-opening reaction of epoxides with nitric oxide

Synthetic Communications

Volumn 36, Issue 21, 2006, Pages 3149-3152

  Fan, Yuan ^a   Shang, Xiaojie ^a   Liu, Zhongquan ^a,b   Wu, Longmin ^a  

^a LANZHOU UNIVERSITY   (China)

^b Academy of Organic Chemistry   (China)

Author keywords

Epoxide; Nitric Oxide; Ring opening

Indexed keywords

EPOXIDE; NITRIC OXIDE; RADICAL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33750202295     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600908769     Document Type: Article

References (7)

1. For reviews, see (a) Yang, D. Ketone-catalyzed asymmetric epoxidation reactions. Acc. Chem. Res. 2004, 37, 497-505;
2. (b) Benjamin, S. L.; Kevin, B. Metal-catalyzed epoxidations of alkenes with hydrogen peroxide. Chem. Rev. 2002, 103, 2457-2473.
3. For review, see Jacobsen, E. N. Asymmetric catalysis of epoxide ring-opening reactions. Acc. Chem. Res. 2000, 33, 421-431.
4. For reviews, see Gansäuer, A.; Lauterbach, T.; Narayan, S. Strained heterocycles in radical chemistry. Angew. Chem. Int. Ed. 2003, 42, 5556-5573.
5. (a) Liu, Z.-Q.; Fan, Y.; Li, R.; Zhou, B.; Wu, L.-M. Regio- and stereoselective ring-opening of aziridines with nitric oxide. Tetrahedron Lett. 2005, 46, 1023-1025;
6. (b) Liu, Z.; Zhou, B.; Liu, Z.; Wu, L. Electrophilic reaction of nitric oxide with Wittig reagents. Tetrahedron Lett. 2005, 46, 1095-1097;
7. Liu, Z.; Li, R.; Yang, D.; Wu, L. Ring-opening of 2,3-epoxy phenyl ketones upon reaction with nitric oxide. Tetrahedron Lett. 2004, 45, 1565-1566.