Opening of Substituted Oxetanes with H2O2 and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4591-4593

  Dussault, Patrick H ^a   Trullinger, Tony K ^a   Noor e Ain, Farhana ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ANTIMALARIAL AGENT; ETHER DERIVATIVE; OXETANE; PEROXIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTIMALARIALS; DIOXOLANES; ETHERS, CYCLIC; PEROXIDES; STEREOISOMERISM;

EID: 0442268762     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0265259     Document Type: Article

References (21)

1. Dussault, P. H.; Liu, X. Org. Lett. 1999, 1, 1391-1393.
2. Oh, C. H.; Kang, J. H. Tetrahedron Lett. 1998, 39, 2771.
3. Feldman, K. S. SynLett 1995, 217-225.
4. Dussault, P. H.; Lee, R.; Lee, H. J.; Schultz, J. A.; Zope, U. R. J. Org. Chem. 2000, 65, 8407-14.
5. Dussault, P. H. In Active Oxygen in Chemistry; Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Blackie A & P: London, 1995; pp 141-203.
6. Adam, W.; Rios, A. J. Chem. Soc. D 1971, 822-823. Higuchi, Y.; Matsuyama, K.; Komai, T. Bull. Chem. Soc. Jpn. 1988, 61, 1821-1823.
7. Adam, W.; Rios, A. J. Chem. Soc. D 1971, 822-823. Higuchi, Y.; Matsuyama, K.; Komai, T. Bull. Chem. Soc. Jpn. 1988, 61, 1821-1823.
8. Xianming, H.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1399-1408.
9. Kropf, H.; Torkler, A. J. Chem. Res., Miniprint 1985, 304.
10. Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109-11.
11. Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B. J. Org. Chem. 1982, 47, 1378-80.
12. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-19.
13. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-15.
14. Picard, P.; LeClerq, D.; Bats, J.-P.; Moulines, J. Synthesis 1981, 550-551.
15. Balsamo, A.; Ceccarelli, G.; Crotti, P.; Macchia, F. J. Org. Chem. 1975, 40, 473-6.
16. 2 was never stored but rather quenched with aqueous sulfite or bisulfite at the end of each work period. Reaction workups employed an aqueous wash prior to any concentration.
17. 2 and low molecular weight hydroperoxides should be treated as potential explosives, and experimenters should follow standard safety precautions, including minimization of scale and avoidance of redox-active metals or their salts: Medard, L. A. Accidental Explosions: Types of Explosive Substances; Ellis Horwood Limited: Chichester, 1989; Vol. 2. Patnaik, P. A Comprehensive Guide to the Hazardous Properties of Chemical Substances; Van Nostrand Reinhold: New York, 1992. Shanley, E. S. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1970; Vol. 3, pp 341-369.
18. 2 and low molecular weight hydroperoxides should be treated as potential explosives, and experimenters should follow standard safety precautions, including minimization of scale and avoidance of redox-active metals or their salts: Medard, L. A. Accidental Explosions: Types of Explosive Substances; Ellis Horwood Limited: Chichester, 1989; Vol. 2. Patnaik, P. A Comprehensive Guide to the Hazardous Properties of Chemical Substances; Van Nostrand Reinhold: New York, 1992. Shanley, E. S. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1970; Vol. 3, pp 341-369.
19. 2 and low molecular weight hydroperoxides should be treated as potential explosives, and experimenters should follow standard safety precautions, including minimization of scale and avoidance of redox-active metals or their salts: Medard, L. A. Accidental Explosions: Types of Explosive Substances; Ellis Horwood Limited: Chichester, 1989; Vol. 2. Patnaik, P. A Comprehensive Guide to the Hazardous Properties of Chemical Substances; Van Nostrand Reinhold: New York, 1992. Shanley, E. S. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1970; Vol. 3, pp 341-369.
20. Dussault, P. H.; Davies, D. R. Tetrahedron Lett. 1996, 37, 463-466.
21. Ushigoe, Y.; Torao, Y.; Masuyama, A.; Nojima, M. J. Org. Chem. 1997, 62, 4949-54.