A novel effective transition metal based salt-catalyzed azidolysis of 1,2-epoxides

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1675-1678

  Crotti, Paolo ^a   Di Bussolo, Valeria ^a   Favero, Lucilla ^a   Macchia, Franco ^a   Pineschi, Mauro ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; AZIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029872653     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00105-0     Document Type: Article

References (17)

1. Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M.; Tetrahedron Lett. 1994, 35, 433-436.
2. Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.;Pineschi, M.Tetrahedron Lett. 1994, 35, 6537-6540.
3. The term "contra-Markovnikov" is preferred to "anti-Markovnikov" in order to avoid confusion with the stereochemical use of the prefix "and" (De La Mare, P.B.D.; Bolton, R. Electrophilic Additions to Unsaturated Systems ; Elsevier Scientific: Amsterdam, 1982).
4. a) Scriven, E.F.V.; Turnbull, K. Chem. Rev. 1988, 88, 297-368.
5. b)The Chemistry of the Azido group, Patai S.; Ed.Wiley; New York, 1971.
6. c) Coe, D.M.; Myers, P.L.; Parry, D.M.; Roberts, S.M.; Storer, R. J.Chem.Soc.Chem.Comm. 1990, 151-153.
7. Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett.. 1990, 31, 5641-5644 and references therein.
8. Van de Weghe, P.; Collin, J. Tetrahedron Lett. 1995, 36, 1649-1652.
9. Hachiya, I.; Moriwaki, M.; Kobayashi, S. Tetrahedron Lett. 1995, 36, 409-412.
10. Li, C.; Arasappan, A.; Fuchs, P.L. Tetrahedron Lett. 1993, 34, 3535-3538.
11. 3CN was preferred, due to the better chemical yields generally obtained with this latter solvent.
12. Papa, A.J. J.Org.Chem. 1966, 31, 1426-1430.
13. 3 catalyzed by ytterbium (III) isopropoxide (Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc. Chem. Comm. 1995, 1021-1022) and by tetraphenylstibonium hydroxide (Fujiwara, M.; Tanaka, M.; Baba, A.; Ando, H.; Souma, Y. Tetrahedron Lett. 1995, 36, 4849-4852).
14. 3 catalyzed by ytterbium (III) isopropoxide (Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc. Chem. Comm. 1995, 1021-1022) and by tetraphenylstibonium hydroxide (Fujiwara, M.; Tanaka, M.; Baba, A.; Ando, H.; Souma, Y. Tetrahedron Lett. 1995, 36, 4849-4852).
15. - nucleophile present in the reaction medium can substitute one or more triflate groups of the catalyst, thus deactivating it.
16. Onaka, M.; Sugita, K.; Izumi, Y. J. Org. Chem. 1989, 54, 1116-1123.
17. 2 under the conditions of ref.6 was repeated by us to give the corresponding azido alcohols (16% yield) in the α:β-attack ratio =37:63.