Diazo Esters Addition to Trifluoropyruvamides: New Access to Highly Functionalized Trifluoromethyl Epoxides and Diazo Compounds

Synlett

Volumn 1997, Issue 7, 1997, Pages 797-798

  El Kaim, Laurent ^a   Ollivier, Cyril ^a  

^a ENSTA PARISTECH   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010541713     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5760     Document Type: Article

References (10)

1. See: Schlosser M., Tetrahedron, 1978, 34, 3-17; Resnati G., Tetrahedron, 1993, 49, 9385-9445.
2. See: Schlosser M., Tetrahedron, 1978, 34, 3-17; Resnati G., Tetrahedron, 1993, 49, 9385-9445.
3. El Kaïm L., Tetrahedron Lett., 1994, 35, 6669-6670.
4. El Kaïm L., Guyoton S., Meyer C., Tetrahedron Lett., 1996, 37, 375-378.
5. M. Regitz, G. Maas, in "Diazo Compounds", Academic Press, London, 1986, 464-481.
6. Osipov S.N., Kolomiets A., Fokin A.V., Izv. Akad. Nauk. SSSR, 1988, 132-136.
7. Burger K., Neuhauser H., Schieslinger C., Chem. Ztg., 1989, 113, 247-249.
8. 13C NMR (50 MHz) : δ 161.9, 158.7. 133.4, 130.6, 129.3, 126.8, 126.3, 123.7, 122.7, 112.6-129.3 (q, J= 278.4 Hz), 62.8, 58.3-60.5 (q, J= 36.8 Hz), 57, 17.2, 13.7.
9. 4 : C. 48.68 ; H. 4.09 ; N, 12.17. Found C, 48.77 ; H, 4.21 ; N, 12.16.
10. α-Diazoalcohols are known to form epoxides by nitrogen elimination under acid catalysis (ref 4 and ref 6 for an example on trifluoromethyl diazoalcohol).