Epoxidations by peracid anions in water: Ambiphilic oxenoid reactivity and stereoselectivity

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2661-2664

  Washington, Ilyas ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; EPOXIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; THERMODYNAMICS;

ANIONS; EPOXY COMPOUNDS; STEREOISOMERISM; THERMODYNAMICS;

EID: 0037043490     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026105j     Document Type: Article

References (31)

1. For a general discussion see: Sawaki, Y. Epoxidation and Hydroxylation. In The Chemistry Hydroxyl, Ether and Peroxide Groups; Patai, S., Ed.; John Wiley and Sons; Sussex, UK, 1993; pp 598-600.
2. Ye, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Org. Chem. 1997, 62, 3748.
3. (a) Nakamura, M.; Tsutsui, N.; Takeda, T. Tetrahedron Lett. 1984, 25, 3231.
4. (b) Fringuelli, F.; Pizzo, F.; Germani, R. Synlett 1991, 475.
5. (c) Fringuelli, F.; Germani, R.; Pizzo, F.; Santinelli, F. J. Org. Chem. 1992, 57, 1198.
6. Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
7. (a) Anderson, W. K.; Veysoglu, T. J. Org. Chem. 1973, 38, 2267.
8. (b) Fringuelli, F.; Pizzo, F.; Germani, R.; Savelli, P. Org. Prep. Proced. Int. 1989, 26, 757.
9. (c) Fringuelli, F.; Pizzo, F.; Germani, R.; Savelli, P. Tetrahedron Lett. 1989, 30, 1427.
10. (d) Imuta, M.; Ziffer, H. J. Org. Chem. 1979, 44, 1351.
11. (a) Curci R.; DiFuria, F. Tetrahedron Lett. 1974, 47, 4085.
12. (b) Curci, R.; DiFuria, F.; Meneghin M. Gazz. Chim. Ital. 1978, 108, 123.
13. (c) Guillermo, M.; Williams, H. J.; Scott, A. I. Synth. Commun. 1996, 26, 2235.
14. Curci R.; Modena, G. Tetrahedron. Lett. 1965, 6, 863.
15. Gillet, J.; Guerret, O.; Tordo, P. Method for preparing β-phosphorus nitroxide radicals using nonhalogenated organic peracids in a biphasic medium. PCT Int Appl. FR2788270, August 13, 2000.
16. a Data, http://daecr1.harvard.edu/pKa/pka.html, December 7, 2001.
17. Jones, P.; Haggett, M. L.; Holden, D.; Robinson, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 443.
18. (a) Apeloig, Y.; Karni, M.; Rappoport, Z. J. Am. Chem. Soc. 1983, 105, 2784 and references therein.
19. (b) Zimmerman, H. Z.; Singer, L.; Thyagarajan, B. S. J. Org. Chem. 1959, 24, 108 and references therein.
20. Porter, N. A.; Yin, H.; Pratt, D. A. J. Am. Chem. Soc. 2000, 122, 11272.
21. -4 hartrees.
22. Studies of performic acid, dioxirane, peroxynitrous acid, and oxaziridine epoxidations have shown that B3LYP/6-31G* calculations provide transition structure and energies in accord with available experimental data and QCI calculations. See: (a) Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147.
23. (b) Bach, D. R.; Glukhovtsev, N. M.; Gonzalez, C. J. Am. Chem. Soc. 1998, 120, 9902.
24. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404.
25. Deubel, D. V. J. Org. Chem. 2001, 66, 3790.
26. Schleyer, P. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Rohde, C.; Arad, D.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 6467.
27. Mohamadi, F.; Still, W. C. Tetrahedron Lett. 1986, 27, 893.
28. 19
29. Palombi, L.; Bonadies, F.; Scettri, A. Tetrahedron, 1997, 53, 11369.
30. 1H NMR spectrum a small doublet peak could be found at 2.6 ppm that had an area of around 2% of the peak found at 2.7 ppm.
31. Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703.