Flexible synthetic approach to a (S)-norcamphor-based hydroperoxide: An efficient oxidant for asymmetric sulfoxidations

European Journal of Organic Chemistry

Volumn , Issue 3, 2006, Pages 713-718

  Lattanzi, Alessandra ^a   Piccirillo, Sandro ^a   Scettri, Arrigo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

(S) norcamphor; Asymmetric synthesis; Kinetic resolution; Optically pure alkyl hydroperoxides; Sulfoxidation

Indexed keywords

EID: 32044445819     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500680     Document Type: Article

References (38)

1. a) T. Tarata, W. Ando, Bull. Chem. Soc. Jpn. 1986, 59, 1275;
2. b) P. H. Dussault, R. J. Lee, J. Am. Chem. Soc. 1994, 116, 4485;
3. c) H.-J. Hamann, E. Höft, D. Mostowicz, A. Mishnev, Z. Urbańczyk-Lipkowska, M. Chmielewski, Tetrahedron 1997, 53, 185;
4. d) W. Adam, M. N. Korb, K. J. Roschmann, C. R. Saha-Moeller, J. Org. Chem. 1998, 63, 3423;
5. e) C. L. Dwyer, C. D. Gill, O. Ichihara, R. J. K. Taylor, Synlett 2000, 5, 704;
6. f) W. Adam, P. B. Rao, H.-G. Degen, C. R. Saha-Möller, J. Am. Chem. Soc. 2000, 122, 5654;
7. g) C. Bolm, O. Beckmann, T. Kuhn, C. Palazzi, W. Adam, B. P. Rao, C. R. Saha-Möller, Tetrahedron: Asymmetry 2001, 12, 2441.
8. a) R. A. Johnson, K. B. Sharpless, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 231;
9. b) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis; Springer; Berlin: 1999;
10. c) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603.
11. a) M. Aoki, D. Seebach, Helv. Chim. Acta 2001, 84, 187;
12. b) W. Adam, P. L. Alsters, R. Neumann, C. R. Saha-Möller, D. Seebach, R. Zhang, Org. Lett. 2003, 5, 725.
13. A. Lattanzi, P. Iannece, A. Vicinanza, A. Scettri, Chem. Commun. 2003, 1440.
14. A. Lattanzi, P. Iannece, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 1779.
15. A. Lattanzi, M. Cocilova, P. Iannece, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 3751.
16. A. Lattanzi, S. Piccirillo, A. Scettri, Eur. J. Org. Chem. 2005, 8, 1669.
17. A. Lattanzi, P. Iannece, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 413.
18. a) P. Barraclough, Tetrahedron Lett. 1980, 21, 1897;
19. b) J. H. Horner, M. Vera, J. B. Grutzner, J. Org. Chem. 1986, 51, 4212;
20. c) G. H. Posner, E. M. Shulman-Roskes, Tetrahedron 1992, 48, 4677;
21. d) W. C. Wong, W. Sun, W. Cui, Y. Chen, C. Forray, P. J.-J. Vaysse, T. A. Brauchek, C. Gluchowski, J. Med. Chem. 2000, 43, 1699.
22. a) S. Ikegami, D. L. Vander Jagt, H. C. Brown, J. Am. Chem. Soc. 1968, 90, 7124;
23. b) H. L. Goering, H. C. Brown, C. B. Schewene, J. Am. Chem. Soc. 1968, 90, 6214;
24. c) D. Lenoir, Y. Apeloig, D. Arad, P. v. R. Schleyer, J. Org. Chem. 1988, 53, 661;
25. d) H. C. Brown, M. Ravindranathan, C. G. Rao, F. J. Chloupek, M.-H. Rei, J. Org. Chem. 1978, 43, 3667;
26. e) C. A. Grob, G. von Sprecher, A. Waldner, Helv. Chim. Acta 1983, 66, 2656.
27. M. Kawamura, K. Ogasawara, Tetrahedron Lett. 1995, 36, 3369.
28. D. A. Lightner, T. D. Bouman, B. V. Crist, S. L. Rodgers, M. A. Knobeloch, A. M. Jones, J. Am. Chem. Soc. 1987, 109, 6248.
29. NOESY experiment on the diastereoisomeric mixture of the alcohols 5 showed correlation peaks between the methyl group at position 3 and the hydrogens on the furyl ring for the most abundant diastereoisomer, thus confirming that these two groups are in a cis relationship. The absence of any peak of correlation for the methyl group with hydrogens on the furyl ring was observed in the case of the minor diastereoisomer, which confirmed that the two groups are in a trans relationship.
30. The tertiary 2′-furyl-2-norbornyl cation was found to be stabilized by the charge-delocalizing ability of the furyl system. It has been reported that there is substantial π-bond character between C-2 of the furyl moiety and the cationic carbon, see: G. A. Olah, A. L. Berrier, G. K. S. Prakash, J. Org. Chem. 1982, 47, 3903.
31. a) I. Fernández, N. Khiar, Chem. Rev. 2003, 103, 3651;
32. b) A. M. Rouhi, Chem. Eng. News 2003, 81, 56;
33. c) J. Legros, J. R. Dehli, C. Bolm, Adv. Synth. Catal. 2005, 347, 19.
34. nd edition (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 479;
35. b) C. Bolm, Coord. Chem. Rev. 2003, 237, 245;
36. c) K. P. Volcho, N. F. Salakhutdinov, A. G. Tolstikov, Russ. J. Org. Chem. 2003, 39, 1537.
37. H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249.
38. Alcohol exo-5 was recovered during the purification procedure (flash chromatography) in 65-75% yield and recycled for the synthesis of 3, thus making the entire process more convenient.