Diastereoselective synthesis of 2,4-disubstituted tetrahydropyranols and ethers via a prins-type cyclization catalyzed by scandium triflate

Tetrahedron

Volumn 56, Issue 16, 2000, Pages 2403-2411

  Zhang, Wen Chun ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

Cyclization; Diastereoselection; Pyrans; Scandium and compounds

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; CHLOROFORM; ETHER DERIVATIVE; SCANDIUM; TETRAHYDROPYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYST; CHEMICAL BOND; CYCLIZATION; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 0034646880     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00152-6     Document Type: Article

References (37)

1. For reviews, see: (a) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 51, 505.
2. (b) Adams, D. R.; Bhatnagar, S. P. Synthesis 1977, 661.
3. (c) Snider, B. B. The Prins and Carbonyl Ene Reactions.
4. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 527-561. Overman has used cation-alkene cyclization extensively in natural product synthesis, for an example, see: Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. For an excellent account on cation-alkene cyclizations, see: Overman, L. E. Acc. Chem. Res. 1992, 25, 352.
5. In Comprehesive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 527-561. Overman has used cation-alkene cyclization extensively in natural product synthesis, for an example, see: Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. For an excellent account on cation-alkene cyclizations, see: Overman, L. E. Acc. Chem. Res. 1992, 25, 352.
6. Nicolaou K.C., Sorensen E.J. Classics in Total Synthesis. 1996;VCH, Weinheim.
7. The best known method in this regard is probably the hetero-Diels-Alder reaction with Danishefsky's Diene, for examples: (a) Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F. J. Am. Chem. Soc. 1984, 106, 2456.
8. (b) Danishefsky, S. J.; Maring, C. J. J. Am. Chem. Soc. 1989, 111, 2193.
9. (a) Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441.
10. (b) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768.
11. (a) Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973.
12. (b) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913.
13. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
14. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
15. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
16. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
17. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
18. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
19. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
20. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
21. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
22. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
23. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
24. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271. For some other related recent examples of Prins-cyclization in forming tetrahydropyrans, see: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141; Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895; Marko, I. E.; Dobbs, A. P.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Marko, I. E. In Novel Trends in Electrorganic Synthesis; Torii, S., Ed.; Springer: Berlin, 1998; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022; Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115; Masuyama, Y.; Gotoh, S.-Y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53.
25. Yi X.H., Haberman J.X., Li C.J. Synth. Commun. 28:1998;2999.
26. Yang J., Viswanathan G.S., Li C.J. Tetrahedron Lett. 40:1999;1627.
27. Zhang W.C., Viswanathan G.S., Li C.J. Chem. Commun. 1999;291.
28. Nishizawa M., Shigaraki T., Takao H., Imagawa H., Sugihara T. Tetrahedron Lett. 40:1999;1153.
29. Cloninger M.J., Overman L.E. J. Am. Chem. Soc. 121:1999;1092.
30. For a leading reference, see: (a) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590.
31. For a related review, see: (b) Kobayashi, S. Synlett 1994, 689; Kobayashi, S. In Organic Synthesis in Water; Grieco, P. A., Ed., Thomson Science: Glasgow 1998; Xie, W.; Jin, Y.; Wang, G. P. Chemtech 1999, 29 (2), 23.
32. For a related review, see: (b) Kobayashi, S. Synlett 1994, 689; Kobayashi, S. In Organic Synthesis in Water; Grieco, P. A., Ed., Thomson Science: Glasgow 1998; Xie, W.; Jin, Y.; Wang, G. P. Chemtech 1999, 29 (2), 23.
33. For a related review, see: (b) Kobayashi, S. Synlett 1994, 689; Kobayashi, S. In Organic Synthesis in Water; Grieco, P. A., Ed., Thomson Science: Glasgow 1998; Xie, W.; Jin, Y.; Wang, G. P. Chemtech 1999, 29 (2), 23.
34. 3 catalyzed allylation of aldehydes with allylsilane, see: Yang, Y.; Wang, M.; Wang, D. Chem. Commun. 1997, 1651.
35. Wigfield D.C., Feiner S. Can. J. Chem. 56:1978;789.
36. Bothner-By A.A., Stephens R.L., Lee J.M., Warren C.D., Jeanloz R.W. J. Am. Chem. Soc. 106:1984;811.
37. Nokami J., Yoshizane K., Matsuura H., Sumida S. J. Am. Chem. Soc. 120:1998;6609.