Ring opening reaction of epoxides with diphenyl phosphorazidate

Tetrahedron Letters

Volumn 40, Issue 39, 1999, Pages 7105-7108

  Mizuno, Masanori ^a,b   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b EISAI CO LTD   (Japan)

Author keywords

Azides; Epoxides; Phosphoric acid; Phosphoric acid derivatives; Vinylation

Indexed keywords

DIPHENYLPHOSPHORAZIDATE; EPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033600692     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01440-9     Document Type: Article

References (11)

1. 1. (a) The Chemistry of the Azido group; Patai, S., Ed.; Wiley: New York, 1971.
2. (b) Scriven, E. F. V; Turnbull, K. Chem. Rev. 1988, 88, 297.
3. 2. Sutowardoyo, K. I.; Emziane, M.; Lhoste, P.; Sinou, D. Tetrahedron 1991, 47, 1435 and references cited therein.
4. 3. (a) Shioiri, T.; Yamada, S. Org. Synth. Col. Vol. VII, 1990, 135.
5. (b) For a review see: Thomas, A. V. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; Vol. 4, pp. 2242-2245.
6. +] 426.1219, found 426.1229.
7. 3, 400 MHz) δ 0.90 (3H, t, J=7.2 Hz), 0.98 (3H, t, J=7.2 Hz), 1.42 (2H, tq, J=7.6, 7.2 Hz), 2.37 (2H, tdd, J=7.6, 6.8, 2.8 Hz), 3.84 (2H, q, J=7.2 Hz), 6.01 (1H, td, J=6.8, 2.8 Hz), 7.37-7.47 (9H, m), 7.68-7.74 (6H, m).
8. 6. (a) L'Abbé, G.; Hassner, A. J. Org. Chem. 1971, 36, 258.
9. (b) Molina, P.; Pastor, A.; Vilaplana, M. J. Tetrahedron Lett. 1993, 34, 3773.
10. 7. (a) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1963, 5288.
11. (b) Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 5641.