Dehydrative reduction: A highly diastereoselective synthesis of syn-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane

Organic Letters

Volumn 5, Issue 5, 2003, Pages 685-688

  Kim, Seongkon ^a   Wu, Jane Y ^a   Chen, Helen Y ^a   DiNinno, Frank ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIOXAN DERIVATIVE; CATECHOL DERIVATIVE; KETONE DERIVATIVE; OXATHIIN DERIVATIVE; THIOPHENOL DERIVATIVE; DIOXANE DERIVATIVE; KETONE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; HYDRATION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATECHOLS; CYCLIZATION; DIOXANES; KETONES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0037529214     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0274763     Document Type: Article

References (53)

1. (a) Boulton, A. J. Compr. Heterocycl. Chem. II 448.
2. (b) Maria, W. Q.; Sayeed, K. T.; Alersandro, P.; Maria, O. G.; Gabriella, M.; Carlo, M. J. Med. Chem. 1993, 35, 1520.
3. (c) Gaster, L. M.; Jenning, A. J. et al. J. Med. Chem. 1993, 36, 4121.
4. (d) Quaglia, W.; Pigini, M.; Giannella, M. J. Med. Chem. 1990, 33, 2946.
5. (e) Melchiorre, C.; Brasili, L.; Giardina, D.; Pigini, M. J. Med. Chem. 1984, 27, 1536.
6. (f) Tanaka, H.; Shibata, M.; Ohira, K.; Ito, K. Chem. Pharm. Bull. 1985, 33, 1419.
7. (g) Fukuyama, Y.; Hasegawa, T.; Toda, M.; Kodama, M.; Okazaki, H. Chem. Pharm. Bull. 1992, 40, 252.
8. (h) Soukri, M.; Lazar, S.; Akssira, M.; Guillaumet, G. Org. Lett. 2000, 2, 1557.
9. (i) Labrosse, J. R.; Lhoste, P.; Sinou, D. Org. lett. 2000, 2, 527.
10. (j) Sweetner; Arnoldi, A.; Bassoli, A.; Merlini, L.; Ragg, E. J. Chem. Soc., Perkin Trans 1. 1993, 1359.
11. (a) Capozzi, G.; Falciani, C.; Menichetti, S.; Nativi, C. J. Org. Chem. 1997, 62, 2611.
12. (b) Tanaka, H.; Shibata, M.; Ohira, K.; Ito, K. Chem. Pharm. Bull. 1985, 33, 1419.
13. (c) Procopiou, P. A.; Brodie, A. C.; Deal, M. J.; Hayman, D. F. Tetrahedron Lett. 1993, 34, 7483.
14. (d) Guz, N. R.; Stermitz, F. R.; Johnson, J. B.; Belson, T. D.; Willen, S.; Hsiang, J. Lewis, K. J. Med. Chem. 2001 44, 261.
15. (e) Li, L.; Hang, T. Org. Lett. 2001, 3, 739.
16. (f) Ganesh, T.; Davidkrupadanam, G. L. Synth. Commum. 1998, 28, 3121.
17. (g) She, X.; Jing, X.; Pan, X.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 1999, 40, 4567.
18. (h) Matsumoto, K.; Takahashi, H.; Miyake, Y.; Fukuyama, Y. Tetrahedron Lett. 1999, 40, 3185.
19. (i) Gu, W.; Jing, X.; Pan, X.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079.
20. (j) Arnoldi, A.; Bassoli, A.; Caputo, R.; Merlini, L.; Palumbo, G.; Pedatella, S. J. Chem. Soc., Perkin Trans. 1 1994, 1241.
21. (k) Tegeler, J.; Org, H. H.; Profih, J. A. J. Heterocycl. Chem. 1983, 20, 867.
22. (a) Nair, V.; Mathew, B. Tetrahedron lett. 2000, 41, 6919.
23. (b) Corsano, S.; Proietti, G.; Castagnino, E.; Strappaghetti, G. Farmaco Ed. Sci. 1982, 38, 265.
24. (c) Schonberg, A.; Awad, W. I.; Mousa, G. A. J. Am. Chem. Soc. 1955, 77, 3850.
25. Kursanov, D. N.; Parnes, Z. N.; Lolm, N. M. Synthesis 1974, 633.
26. (a) Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2000, 122, 168.
27. (b) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1,447.
28. (c) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
29. (d) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043.
30. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
31. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
32. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
33. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
34. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
35. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
36. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
37. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
38. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
39. 1,3-Stereoselectivity: (a) Colobert, F.; Mazery, R. D.; Solladie, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Ghosh, A.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027. (c) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542. (d) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208. (e) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (f) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245. (g) Mukaiyama, T.; Shimpuku, T.; Takashima, T.; Kobayashi, S. Chem. Lett. 1989, 145. (h) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983, 209. (i) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (j) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032.
40. 1,2 strain; see: (a) Kraus, G. A.; Molina, M. T.; Walling, J. A. J. Chem. Soc., Chem. Commum. 1986, 1568. (b) Kraus, G. A.; Molina, M. T.; Walling, J. A. J. Org. Chem. 1987, 52, 1273.
41. 1,2 strain; see: (a) Kraus, G. A.; Molina, M. T.; Walling, J. A. J. Chem. Soc., Chem. Commum. 1986, 1568. (b) Kraus, G. A.; Molina, M. T.; Walling, J. A. J. Org. Chem. 1987, 52, 1273.
42. -1 (see: Shtsuka, Y.; Oishi, T. Chem. Pharm. Bull. 1983, 31, 443).
43. For 5b, the major tautomeric form would be 5b-I (see: Dzvinchuk, I. B.; Lozinskii, M. O. Zh. Org. Khim. 1991, 27, 560).
44. (a) Ganesh, T.; Kumar, H.; Krupadanam, G. L. Synth. Commum. 1999, 29, 2069 and references therein
45. The functionalized thiophenols 3 were prepared by the known procedure with minor modifications. (b) Werner, G.; Biebrich, W. U.S. Patent 2,276,553; 2,332,418. (c) Hanzlik, R. P.; Weller, P. E.; Desai, J.; Zheng, J.; Hall, L. R. ; Slaughter, D. E. J. Org. Chem. 1990, 55, 2736.
46. The functionalized thiophenols 3 were prepared by the known procedure with minor modifications. (b) Werner, G.; Biebrich, W. U.S. Patent 2,276,553; 2,332,418. (c) Hanzlik, R. P.; Weller, P. E.; Desai, J.; Zheng, J.; Hall, L. R. ; Slaughter, D. E. J. Org. Chem. 1990, 55, 2736.
47. The coupling constant for the trans isomers in related compounds is in the range of 7-9 Hz, while the cis isomers exhibit couplings of 2-3 Hz (see refs 1g, 2b, and: Pfundt, G.; Farid, S. Tetrahedron 1966, 22, 2237). The trans isomer that was independently synthesized (see ref 2j) exhibited a large coupling constant (J = 9.0 Hz) for H2,3.
48. In contrast, hydrogenation of the analogous benzoxathiin returned only starting material (>90%), even at high pressures, presumably due to catalyst poisoning by the sulfur atom.
49. (a) Adam, W. et al. J. Org. Chem. 1984, 49, 3920.
50. (b) Procopiou, P. A. et al. Tetrahedron Lett. 1993, 34, 7483.
51. +), 359.
52. For the preparation of the fluoro-substituted thiophenol 3h, see: Watanabe, M.; Date, M.; Tsukazake, M.; Furukawa, S. Chem. Pharm. Bull. 1989, 37, 36.
53. We have shown that this product does not arise from the starting material 5. For example, exposure of the silylated ketone, corresponding to entry 8 in Table 2, to the reaction conditions or at higher temperatures ranging from zero degrees to room temperature failed to yield any appreciable quantity of the analogous reduction product. Related experiments have also eliminated the product as the source and suggest the involvement of an intermediate leading to the oxonium species as the potential source.