Asymmetric electrophilic methoxyselenenylations and cyclizations with 3- camphorseleno derivatives

Tetrahedron

Volumn 55, Issue 11, 1999, Pages 3191-3208

  Back, Thomas G ^a   Dyck, Brian P ^a   Nan, Siqiao ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR DERIVATIVE; DISELENIDE; SELENIDE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; CYCLIZATION; DIASTEREOISOMER; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033105284     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01133-8     Document Type: Article

References (44)

1. Schmid, G.H.; Garratt, D.G. In The Chemistry of Double-bonded Functional Groups. Supplement A, Part 2; Patai S., Ed.; Wiley: New York, 1977; Chapter 9.
2. For reviews of electrophilic selenium reactions, see: (a) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; Chapter 7.
3. (b) Back T.G. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley: New York, 1987; Chapter 1.
4. (c) Back, T.G. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; Wiley: Chichester, 1987; Volume 2, Chapter 3.
5. For examples of anti-Markovnikov additions of selenenyl chlorides under kinetic conditions, see: (a) Raucher, S. J. Org. Chem. 1977, 42, 2950.
6. (b) Ho, P.-T.; Kolt, R.J. Can. J. Chem. 1982, 60, 663.
7. For reviews, see: (a) Reference 2a; Chapter 8.
8. (b) Nicolaou, K.C.; Petasis, N.A.; Claremon, D.A. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley: New York, 1987; Chapter 2.
9. (c) Nicolaou K.C.; Petasis, N.A. In Selenium in Natural Products Synthesis; CIS: Philadelphia, 1984; Chapter 7.
10. (a) Clive, D.L.J.; Chittattu, G.; Curtis, N.J.; Kiel, W.A.; Wong, C.K. J. Chem. Soc., Chem. Commun. 1977, 725.
11. (b) Clive, D.L.J.; Russell, C.G.; Chittattu, G.; Singh, A. Tetrahedron 1980, 36, 1399.
12. (a) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Tetrahedron 1997, 53, 2029.
13. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Tetrahedron Lett. 1995, 36, 5219.
14. (c) Fujita, K.; Iwaoka, M.; Tomoda, S. Chem. Lett. 1994, 923.
15. (d) Fujita, K.; Iwaoka, M.; Tomoda, S. Chem. Lett. 1992, 1123.
16. (e) Tomoda, S.; Fujita, K.; Iwaoka, M. J. Chem. Soc., Chem. Commun. 1990, 129.
17. (f) Tomoda, S.; Iwaoka, M. Chem. Lett. 1988, 1895.
18. (g) Déziel, R.; Malenfant, E.; Thibault, C.; Fréchette, S.; Gravel, M. Tetrahedron Lett. 1997, 38, 4753.
19. (h) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619.
20. (i) Fukuzawa, S.; Takahashi, K.; Kato, H.; Yamazaki, H. J. Org. Chem. 1997, 62, 7711.
21. (j) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403.
22. (k) Wirth, T.; Fragale, G.; Spichty, M. J. Am. Chem. Soc. 1998, 120, 3376.
23. (l) Wirth, T.; Häuptli, S.; Leuenberger, M. Tetrahedron Asymmetry 1998, 9, 547.
24. (m) Wirth, T.; Fragale, G. Synthesis 1998, 162.
25. (n) Wirth, T.; Fragale, G. Chem. Eur. J. 1997, 3, 1894.
26. (o) Wirth, T.; Angew. Chem. Int. Ed. Engl. 1995, 34, 1726.
27. (a) Nishibayashi, Y.; Srivastava, S.K.; Takada, H.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 2321.
28. (b) Fujita, K.; Murata, K.; Iwaoka, M. ; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641.
29. (c) Déziel, R.; Malenfant, E. J. Org. Chem. 1995, 60, 4660.
30. Back, T.G.; Dyck, B.P.; Parvez, M. J. Org. Chem. 1995, 60, 703.
31. (a) Preliminary communication: Back, T.G.; Nan, S. J. Chem. Soc., Perkin Trans. 1 (in Press).
32. (b) Preliminary communication: Back, T.G.; Dyck, B.P.J. Chem. Soc., Chem. Commun. 1996, 2567.
33. Subsequently to our report of the preparation of diselenide 1a (réf. 8) and its use in asymmetric cyclizations (réf. 9b), an independent report appeared on the use of a selenenyl sulfate derived from 1a in asymmetric methoxyselenenylations: Tiecco, M.; Testaferri, L.; Santi, C.; Marini, F.; Bagnoli, L.; Temperini, A. Tetrahedron Lett. 1998, 39, 2809.
34. Few protecting groups have been reported for selenols arid diselenides; for recent examples, see: Reinerth, W.A.; Tour, J.M. J. Org. Chem. 1998, 63, 2397.
35. For a review of [2,3]sigmatropic rearrangements of allylic selenoxides, see: Reich, H.J. In Organo- Selenium Chemistry; Liotta, D., Ed.; Wiley: New York, 1987; Chapter 8.
36. (a) Back, T.G.; Dyck, B.P. J. Am. Chem. Soc. 1997, 119, 2079.
37. (b) Back, T.G.; Dyck, B.P.; Nan, S.; Parvez, M. Acta Cryst. 1998, C54, 425.
38. Selenenic acids (RSeOH) are unstable and disproportionate to seleninic acids (RSeOjH) and diselenides (RSeSeR): (a) Reich, H.J.; Wollowitz, S.; Trend, J.E.; Chow, F.; Wendelborn, D.F. J. Org. Chem. 1978, 43, 1697.
39. (b) Hori, T.; Sharpless, K.B. J. Org. Chem. 1978, 43, 1689.
40. Clive, D.L.J.; Chittattu, G.J.; Farina, V.; Kiel, W.A.; Menchen, S.M.; Russell, C.G.; Singh, A.; Wong, C.K.; Curtis, N.J. J. Am. Chem. Soc. 1980, 102, 4438.
41. The cyclization of trans- and cis-4-hexen-1-ols with PhSeCl results in endo- and eto-cyclization, respectively, in the absence ofp-toluenesulfonic acid: Konstantinovic, S.; Bugarcic, Z.; Milosavljevic, S.; Schroth, G.; Mihailovic, M.L. Liebigs Ann. Chem. 1992, 261.
42. Dictionary of Organic Compounds, 6th Edition; Cadogan, J.I.G.; Ley, S.V.; Pattenden, G., Eds.; Chapman and Hall: London, 1996, Volume 6, p. 5835-5836, entry T001299.
43. Mori, K. Tetrahedron 1975, 31, 3011.
44. Dicks, P.F.; Glover, S.A.; Goosen, A.; McCleland, C.W. Tetrahedron 1987, 43, 923.