Auxiliary controlled singlet-oxygen ene reactions of cyclohexenes

Tetrahedron

Volumn 62, Issue 46, 2006, Pages 10639-10646

  Fudickar, Werner ^a   Vorndran, Katja ^a   Linker, Torsten ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

Auxiliary control; Regioselectivity; Singlet oxygen; Stereoselectivity

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ALCOHOL; CYCLOHEXANONE; CYCLOHEXENE DERIVATIVE; HYDROPEROXIDE; SINGLET OXYGEN; TARTARIC ACID;

ARTICLE; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; ENANTIOMER; MOLECULAR INTERACTION; PRIORITY JOURNAL; REDUCTION KINETICS; STEREOSPECIFICITY;

EID: 33749236107     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.104     Document Type: Article

References (36)

1. Recent reviews:
2. Clennan E.L. Tetrahedron 56 (2000) 9151-9179
3. Clennan E.L., and Pace A. Tetrahedron 61 (2005) 6665-6691
4. Excellent review:. Stratakis M., and Orfanopoulos M. Tetrahedron 56 (2000) 1595-1615
5. Li X., and Ramamurthy V. J. Am. Chem. Soc. 118 (1996) 10666-10667
6. Clennan E.L., and Sram J.P. Tetrahedron Lett. 40 (1999) 5275-5278
7. Stratakis M., and Froudakis G. Org. Lett. 2 (2000) 1369-1372
8. Bartoschek A., El-Idreesy T.T., Griesbeck A.G., Höinck L.-O., Lex J., Miara C., and Neudörfl J.M. Synthesis (2005) 2433-2444
9. Excellent review:. Prein M., and Adam W. Angew. Chem., Int. Ed. 35 (1996) 477-494
10. Dussault P.H., Woller K.R., and Hillier M.C. Tetrahedron 50 (1994) 8929-8940
11. Adam W., Güthlein M., Peters E.-M., Peters K., and Wirth T. J. Am. Chem. Soc. 120 (1998) 4091-4093
12. Adam W., Peters K., Peters E.-M., and Schambony S.B. J. Am. Chem. Soc. 123 (2001) 7228-7232
13. Adam W., Bosio S.G., and Turro N.J. J. Am. Chem. Soc. 124 (2002) 8814-8815
14. Adam W., Bosio S.G., Turro N.J., and Wolff B.T. J. Org. Chem. 69 (2004) 1704-1715
15. Sundén H., Engqvist M., Casas J., Ibrahem I., and Córdova A. Angew. Chem., Int. Ed. 43 (2004) 6532-6535
16. Córdova A., Sundén H., Engqvist M., Ibrahem I., and Casas J. J. Am. Chem. Soc. 126 (2004) 8914-8915
17. Fudickar W., Fery A., and Linker T. J. Am. Chem. Soc. 127 (2005) 9386-9387
18. Dang H.-S., and Davies A.G. Tetrahedron Lett. 32 (1991) 1745-1748
19. Maldotti A., Andreotti L., Molinari A., Borisov S., and Vasil'ev V. Chem.-Eur. J. 7 (2001) 3564-3571
20. Linker T., and Fröhlich L. Angew. Chem., Int. Ed. Engl. 33 (1994) 1971-1972
21. Linker T., and Fröhlich L. J. Am. Chem. Soc. 117 (1995) 2694-2697
22. Linker T., Rebien F., and Tóth G. Chem. Commun. (1996) 2585-2586
23. Nardello V., Aubry J.-M., and Linker T. Photochem. Photobiol. 70 (1999) 524-530
24. Fröhlich L., and Linker T. Synlett (2004) 2725-2727
25. Alexakis A., and Mangney P. Tetrahedron: Asymmetry 1 (1990) 477-511
26. Johnson R.A., and Sharpless K.B. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis (1993), VCH, New York, NY 101-158
27. Gawronski J., and Gawronska K. Tartaric and Malic Acids in Synthesis (1999), Wiley, New York, NY
28. Ukaji Y., and Inomata K. Synlett (2003) 1075-1087
29. Greene T.W., and Wuts P.G.M. Protecting Groups in Organic Synthesis. 3rd ed. (1999), Wiley, New York, NY
30. Fioravanti S., Luna G., Pellacani L., and Tardella P.A. Tetrahedron 53 (1997) 4779-4786
31. Mash E.A., and Nelson K.A. Tetrahedron 43 (1987) 679-692
32. Mash E.A., Nelson K.A., and Heidt P.C. Tetrahedron Lett. 28 (1987) 1865-1868
33. Mash E.A., Hemperly S.B., Nelson K.A., Heidt P.C., and Van Deusen S. J. Org. Chem. 55 (1990) 2045-2055
34. Tsangarakis C., Zaravinos I.-P., and Stratakis M. Synlett (2005) 1857-1860
35. Gebauer O., and Brückner R. Liebigs Ann. Chem. (1996) 1559-1563
36. March P., Escoda M., Figueredo M., Font J., Garcia-Garcia E., and Rodriguez S. Tetrahedron: Asymmetry 11 (2000) 4473-4483