Diastereoselective synthesis of multisubstituted thiacyclohexanes via cation-olefin cyclizations

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1321-1325

  Yang, Xiao Fan ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CATION; CYCLOHEXANE DERIVATIVE; INDIUM CHLORIDE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034716507     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02299-6     Document Type: Article

References (39)

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11. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
12. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
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14. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
15. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
16. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
17. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
18. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
19. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
20. For examples, see: Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydr. Res. 1998, 308, 297; Izumi, Masayuki, S.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811; Bozo, E.; Boros, S.; Kuszumann, J. Carbohydr. Res. 1997, 302, 149; Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Hausner, E. A.; Meunier, P. C.; Munzer, D. A.; Stoltenborg, J. K.; Gillies, P. J.; Burcham, D. L., et al. Bioorg. Med. Chem. 1996, 4, 1493; Tsuruta, O.; Yuasa, H.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1996, 6, 1989; Belleau, B.; Gulini, U.; Gour-Salin, B.; Ahmed, F. R. Can. J. Chem. 1985, 63, 1268; Lane, S.; Taylor, R. J. K. Tetrahedron Lett. 1985, 26, 2821; McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675; Kawai, S. H.; Chin, J.; Just, G. Carbohydr. Res. 1991, 211, 245; Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLay, I. M.; Jordan, R.; Mason, J. S.; Palfrey, M. N.; Walsh, R. J. A., et al. J. Med. Chem. 1992, 35, 3613; Izquierdo-Cubero, I.; Lopez-Espinosa, M. T. P.; Richardson, A. C.; Suarez, O. M. D. Carbohydr. Res. 1993, 242, 109; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1994, 72, 208; Ghosh, A. K.; Thompson, W. J.; Munson, P. M.; Liu, W.; Huff, J. R. Bioorg. Med. Chem. Lett. 1995, 5, 83; Mehta, S.; Andrews, J. S.; Svensson, B.; Mario, P. B. J. Am. Chem. Soc. 1995, 117, 9783.
21. Block, E. Reactions of Organosulfur Compounds; Academic Press: New York, 1978; Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H. J. Am. Chem. Soc. 1981, 103, 3210.
22. Block, E. Reactions of Organosulfur Compounds; Academic Press: New York, 1978; Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H. J. Am. Chem. Soc. 1981, 103, 3210.
23. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
24. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
25. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
26. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
27. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
28. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
29. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
30. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
31. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
32. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
33. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
34. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
35. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
36. For a recent review on Prins-type reactions, see: Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561. For a related cyclization to form tetrahydropyran derivatives mediated by Lewis acids, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 973; Chan, T. H.; Arya, P. Tetrahedron Lett. 1989, 30, 4065; Metzger, J. O.; Biermann, U. Bull. Soc. Chim. Belg. 1994, 103, 393; Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141; Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895; Semeyn, C.; Blaauw, R. H. Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426; Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271; Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092; Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; Zhang, W. C.; Viswanathan, G. S.; Li, C. J. Chem. Commun. (Cambridge) 1999, 291; Samoshin, V. V.; Gremyachinskiy, D. E.; Gross, P. H. Mendeleev Commun. 1999, 53; Nishizawa, M.; Shigaraki, T.; Takao, H.; Imagawa, H.; Sugihara, T. Tetrahedron Lett. 1999, 40, 1153.
37. Mitsunobu, O. Synthesis 1981, 1.
38. Nishio, T. J. Chem. Soc., Perkin Trans. 1 1993, 1113.
39. A typical experimental procedure was as follows: Indium(III) chloride (265 mg, 1.2 mmol) was added to a mixture of benzaldehyde (212 mg, 2.0 mmol) and cis-3-nonen-1-thiol (158 mg, 1.0 mmol) in 25 mL methylene chloride which was pre-dried with 4 Å MS overnight. After being stirred at room temperature for 10 h, the mixture was concentrated. Column chromatography of the crude reaction mixture on silica gel (eluting with hexane) gave 220 mg (78%) of 4-chloro-3-pentyl-2-phenylthiacyclohexane (d.e.=7:1) as a colorless oil.