Intrazeolite photooxygenation of chiral alkenes. Control of facial selectivity by confinement and cation-π interactions

Tetrahedron

Volumn 62, Issue 46, 2006, Pages 10623-10632

  Stratakis, Manolis ^a   Raptis, Christos ^a   Sofikiti, Nikoletta ^a   Tsangarakis, Constantinos ^a   Kosmas, Giannis ^a   Zaravinos, Ioannis Panagiotis ^a   Kalaitzakis, Dimitris ^a   Stavroulakis, Dimitris ^a   Baskakis, Constantinos ^a   Stathoulopoulou, Aggeliki ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

Cation interactions; Diastereoselection; Hydroperoxides; Regioselectivity; Singlet oxygen; Zeolites

Indexed keywords

ALKENE; CATION; DEUTERIUM; SODIUM; ZEOLITE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHIRALITY; COMPARATIVE STUDY; MOLECULAR INTERACTION; PHASE TRANSITION; PHOTOOXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 33749253168     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.102     Document Type: Article

References (39)

1. Wasserman H.H., and Murray R.W. Singlet Oxygen (1979), Academic, New York, NY
2. For a recent review article, see:. Clennan E.L., and Pace A. Tetrahedron 61 (2005) 6665-6691
3. Wahlen J., de Vos D.E., Jacobs P.A., and Alsters P.L. Adv. Synth. Catal. 346 (2004) 152-164
4. Tung C.-H., Wu L.-Z., Zhang L.-P., and Chen B. Acc. Chem. Res. 36 (2003) 39-47
5. Tung C.-H., Wang H., and Ying Y.-M. J. Am. Chem. Soc. 120 (1998) 5179-5186
6. Chen Y.-Z., Wu L.-Z., Zhang L.-P., and Tung C.-H. J. Org. Chem. 70 (2005) 4676-4681
7. Tung C.-H., and Guan J.-Q. J. Am. Chem. Soc. 120 (1998) 11874-11879
8. Tung C.-H., Wu L.Z., Zhang L.P., Li H.R., Yi X.Y., Ming K.S., Yuan Z.Y., Guan J.Q., Wang H.W., Ying Y.M., and Xu X.H. Pure Appl. Chem. 72 (2000) 2289-2298
9. Ramamurthy V., Lakshminarasimhan P., Grey C.P., and Johnston L.J. Chem. Commun. (1998) 2411-2424
10. Sen S.E., Smith S.M., and Sullivan K.A. Tetrahedron 55 (1999) 12657-12698
11. Stratakis M. Curr. Org. Synth. 2 (2005) 281-299
12. Li X., and Ramamurthy V. J. Am. Chem. Soc. 118 (1996) 10666-10667
13. Pace A., and Clennan E.L. J. Am. Chem. Soc. 124 (2002) 11236-11237
14. Jockusch S., Sivaguru J., Turro N.J., and Ramamurthy V. Photochem. Photobiol. Sci. 4 (2005) 403-405
15. Robbins R.J., and Ramamurthy V. Chem. Commun. (1997) 1071-1072
16. Stratakis M., and Froudakis G. Org. Lett. 2 (2000) 1369-1372
17. Clennan E.L., and Sram J.P. Tetrahedron 56 (2000) 6945-6950
18. Stratakis M., Nencka R., Rabalakos C., Adam W., and Krebs O. J. Org. Chem. 67 (2002) 8758-8763
19. Stratakis M., Rabalakos C., Mpourmpakis G., and Froudakis G.E. J. Org. Chem. 68 (2003) 2839-2843
20. Ramamurthy V., Shailaja J., Kaanumalle L.S., Sunoj R.B., and Chandrasekhar J. Chem. Commun. (2003) 1987-1999
21. Prein M., and Adam W. Angew. Chem., Int. Ed. 35 (1996) 477-494
22. Rao V.J., Uppili S.R., Corbin D.R., Schwarz S., Lustig S.R., and Ramamurthy V. J. Am. Chem. Soc. 120 (1998) 2480-2481
23. Joy A., Uppili S., Netherthon M.R., Scheffer J.R., and Ramamurthy V. J. Am. Chem. Soc. 122 (2000) 728-729
24. 2=tert-butyl(2,4,5,5-tetramethyl-2-hexene) affords a ratio erythro/threo secondary allylic hydroperoxides=71/29 (see Ref. 19). This diastereomeric ratio is lower compared to the erythro/threo ratio obtained from the photooxygenation of 3.
25. Adam W., and Nestler B. Liebigs Ann. Chem. (1990) 1051-1053
26. Adam W., Brunker H.-G., Kumar A.S., Peters E.-M., Peters K., Schneider U., and von Schnering H.G. J. Am. Chem. Soc. 118 (1996) 1899-1905
27. Karabatsos G.J. J. Am. Chem. Soc. 89 (1967) 1367-1371 and references cited therein
28. A preliminary account for the intrazeolite photooxygenation of the phenyl-substituted alkenes 1-3 has been published:. Stratakis M., Kalaitzakis D., Stavroulakis D., Kosmas G., and Tsangarakis C. Org. Lett. 5 (2003) 3471-3474
29. Feller D. Chem. Phys. Lett. 322 (2000) 543-548
30. +-benzene interaction. Ma J.C., and Dougherty D.A. Chem. Rev. 97 (1997) 1303-1324
31. Clennan E.L., Sram J.P., Pace A., Vincer K., and White S. J. Org. Chem. 67 (2002) 3975-3978
32. Stratakis M., and Kosmas G. Tetrahedron Lett. 42 (2001) 6007-6009
33. 3 yielded 3-cyclohexyl-3-phenylpropan-1-ol, which was oxidized with PCC to form 3-cyclohexyl-3-phenylpropanal. Finally, Wittig coupling of the aldehyde with isopropylidenetriphenylphosphorane afforded 7.
34. Orfanopoulos M., and Smonou I. Synth. Commun. 18 (1988) 833-839
35. Gollnick K., and Schade G. Tetrahedron Lett. 11 (1973) 857-860
36. Stratakis M., Sofikiti N., Baskakis C., and Raptis C. Tetrahedron Lett. 45 (2004) 5433-5436
37. For the definition of the terminology twin and twix, see:. Adam W., Bottke N., and Krebs O. J. Am. Chem. Soc. 122 (2000) 6791-6792
38. Stratakis M., and Orfanopoulos M. Tetrahedron 56 (2000) 1595-1615
39. Olah G.A., and Arvanaghi M. Angew. Chem., Int. Ed. Engl. 20 (1981) 878-879