Convenient synthesis of highly optically active 2,3,4,6-tetrasubstituted tetrahydropyrans via Prins cyclization reaction (PCR) of optically active homoallylic alcohols with aldehydes

Tetrahedron

Volumn 62, Issue 11, 2006, Pages 2471-2483

  Kataoka, Kazuhide ^a   Ode, Yosuke ^a   Matsumoto, Masashi ^a   Nokami, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Enantiomeric excess; Nucleophile; Prins cyclization reaction

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OPTIC NERVE; PRIMED IN SITU LABELING; PRIORITY JOURNAL; SYNTHESIS;

EID: 32644432747     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.054     Document Type: Article

References (44)

1. For a review, see: (a) T.L.B. Boivin Tetrahedron 43 1987 3309 3362
2. For recent reports on the synthesis of substituted THP ring functionalities in newly discovered bioactive natural compounds, see: (b) J.D. White, P.R. Blakemore, C.C. Browder, J. Hong, C.M. Lincoln, P.A. Nagomyy, L.A. Robarge, and D.J. Wardrop J. Am. Chem. Soc. 123 2001 8593 8595
3. T. Deba, F. Yakushiji, M. Shindo, and K. Shishido Synlett 2003 1500 1502
4. B.R. Graetz, and S.D. Rychnovsky Org. Lett. 5 2003 3357 3360
5. S.H. Kang, H.-w. Choi, C.M. Kim, H.-S. Jun, S.Y. Kang, J.W. Jeong, and J.-H. Youn Tetrahedron Lett. 44 2003 6817 6819
6. I. Paterson, and C.A. Luckhurst Tetrahedron Lett. 44 2003 3749 3754
7. D.R. Williams, D.C. Ihle, and S.V. Plummer Org. Lett. 3 2001 1383 1386
8. T.A. Kirkland, J. Colucci, L.S. Geraci, M.A. Marx, M. Schneider, D.E. Kaelin Jr., and S.F. Martin J. Am. Chem. Soc. 123 2001 12432 12433
9. K. Fujiwara, S. Amano, T. Oka, and A. Murai Chem. Lett. 1994 2147 2150
10. I.E. Markó, R. Dumeunier, C. Leclerq, B. Lero, J.-M. Plancher, A. Mekhalfia, and D.J. Baystom Synthesis 2002 958
11. M.C. Elliot J. Chem. Soc., Perkin Trans. 1 2002 2301
12. Synthesis of tetra- and di-hydropyran derivatives by an acid-catalyzed Prins-type cyclization reaction of homoallylic alcohol with aldehydes: (c) X.-F. Yang, J.T. Mague, and C.-J. Li J. Org. Chem. 66 2001 739 747 and references cited therein
13. A. Gambaro, A. Boaretto, D. Marton, and G. Tagliavini J. Organomet. Chem. 254 1983 293 304
14. A. Boaretto, D. Marton, and G. Tagliavini Inorg. Chim. Acta 77 1983 L153 L154
15. A. Gambaro, D. Furlani, D. Marton, and G. Tagliavini J. Organomet. Chem. 299 1986 157 167
16. Z.Y. Wei, J.S. Li, D. Wang, and T.H. Chan Tetrahedron Lett. 28 1987 3441 3444
17. Z.Y. Wei, D. Wang, J.S. Li, and T.H. Chan J. Org. Chem. 54 1989 5768 5774
18. L. Coppi, A. Ricci, and M. Taddei Tetrahedron Lett. 28 1987 973 976
19. L. Coppi, A. Ricci, and M. Taddei J. Org. Chem. 53 1988 911 913
20. A. Mekhalfia, E.I. Markó, and H. Adams Tetrahedron Lett. 32 1991 4783 4786
21. I.E. Markó, and A. Mekhalfia Tetrahedron Lett. 33 1992 1799 1802
22. I.E. Markó, and F. Chellé Tetrahedron Lett. 38 1997 2895 2898
23. R.W. Hoffman, V. Giesen, and M. Fuest Liebigs Ann. Chem. 1993 629 639
24. M. Nishizawa, T. Shigaraki, H. Takao, H. Imagawa, and T. Sugihara Tetrahedron Lett. 40 1999 1153 1156
25. J. Yang, S. Viswanathan, and C.-J. Li Tetrahedron Lett. 40 1999 1627 1630
26. G.S. Viswanathan, J. Yang, J. Yang, and C.-J. Li Org. Lett. 1 1999 993 995
27. C.C.K. Keh, V.V. Namboodiri, R.S. Varma, and C.-J. Li Tetrahedron Lett. 43 2002 4993 4996
28. C. Barry, S.R. Crosby, J.R. Harding, R.A. Hughes, C.D. King, G.D. Parker, and C.L. Willis Org. Lett. 5 2003 2429 2432
29. K.-P. Chan, and T.-P. Loh Org. Lett. 7 2005 4491 4494
30. G. Sabitha, K.B. Reddy, G.S.K.K. Reddy, N. Fatima, and J.S. Yadav Synlett 2005 2347 2351
31. X.-F. Yang, M. Wang, Y. Zhang, and C.-J. Li Synlett 2005 1912 1916
32. S.R. Crosby, J.R. Harding, C.D. King, G.D. Parker, and C.L. Willis Org. Lett. 4 2002 577 580
33. S.R. Crosby, J.R. Harding, C.D. King, G.D. Parker, and C.L. Willis Org. Lett. 4 2002 3407 3410
34. D.J. Hart, and C.E. Bennett Org. Lett. 5 2003 1499 1502
35. S. Marumoto, J.J. Jaber, J.P. Vitale, and S.D. Rychnovsky Org. Lett. 4 2002 3919 3922
36. J. Nokami, K. Yoshizane, H. Matsuura, and S. Sumida J. Am. Chem. Soc. 120 1998 6609 6610
37. S. Sumida, M. Ohga, J. Mitani, and J. Nokami J. Am. Chem. Soc. 122 2000 1310 1313
38. J. Nokami, L. Anthony, and S. Sumida Chem. Eur. J. 6 2000 2909 2913
39. J. Nokami, M. Ohga, H. Nakamoto, T. Matsubara, I. Hussain, and K. Kataoka J. Am. Chem. Soc. 123 2001 9168 9169
40. J. Nokami, K. Nomiyama, S. Matsuda, N. Imai, and K. Kataoka Angew. Chem., Int. Ed. 42 2003 1273 1275
41. J. Nokami, K. Nomiyama, S.M. Shafi, and K. Kataoka Org. Lett. 6 2004 1261 1264
42. S.M. Shafi, S. Chou, K. Kataoka, and J. Nokami Org. Lett. 7 2005 2957 2960
43. We can assume that Ts2 is more stable than Ts3, because the internal olefin in Ts2 is thermodynamically more stable than the external olefin in Ts3, and Ts2 is sterically less hindered than Ts3.
44. E.H. Al-Mutairi, S.R. Crosby, J. Darzi, J.R. Harding, R.A. Hughes, C.D. King, T.J. Simpson, R.W. Smith, and C.L. Willis Chem. Commun. 2001 835 836