Reductive cyclizations of hydroxysulfinyl ketones: Enantioselective access to tetrahydropyran and tetrahydrofuran derivatives

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7779-7787

  Carreño, M Carmen ^a   Des Mazery, Renaud ^a,b   Urbano, Antonio ^a   Colobert, Françoise ^b   Solladié, Guy ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; ESTERS; REDUCTION;

ENANTIOMERS;

KETONES;

(6 METHYLTETRAHYDROPYRAN 2 YL)ACETIC ACID; CENTROLOBINE; HETEROCYCLIC COMPOUND; HYDROXYSULFINYL KETONE; KETONE DERIVATIVE; NATURAL PRODUCT; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION; SUBSTITUTION REACTION;

EID: 0141766891     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034817x     Document Type: Article

References (91)

1. For reviews, see: (a) Alvarez, E.; Candenas, M. L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980.
2. (b) Shimizu, Y. M. Chem. Rev. 1993, 93, 1685-1698.
3. (c) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
4. (d) Perron, F.; Albizati, K. M. Chem. Rev. 1989, 89, 1617-1661.
5. For a series of review articles on synthesis of saturated oxygen heterocycles, see: (a) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 2002, 2301-2323.
6. (b) Elliott, M. C.; Williams, E. J. Chem. Soc., Perkin Trans. 1 2001, 2303-2340.
7. (c) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 2000, 1291-1318.
8. (d) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175-4200.
9. (e) Elliott, M. C. Contemp. Org. Synth. 1997, 4, 238-259.
10. (f) Burns, C. J.; Middleton, D. S. Contemp. Org. Synth. 1996, 3, 229-242.
11. (g) Elliott, M. C. Contemp. Org, Synth. 1994, 1, 457-474.
12. (a) Sassaman, M. B.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1988, 44, 3371-3380.
13. (b) Sassaman, M. B.; Kotian, K. D.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1987, 52, 4314-4319.
14. (a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E.; Nugiel, D. A.; Abe, Y. ; Reddy, K. Bal; DeFrees, S. A.; Reddy, D. R.; Awartani, R. A.; Conley, S. R.; Rutjes, F. P. J. T.; Theodorakis, E. A. J. Am. Chem. Soc. 1995, 117, 10227-10238.
15. (b) Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136-4137.
16. González, I.; Forsyth, C. J. J. Am. Chem. Soc. 2000, 122, 9099-9108.
17. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
18. (b) Solladié, G.; Carreño, M. C. In Organosulphur Chemistry: Synthetic Aspects; Page, P. C. B., Ed.; Academic Press: New York, 1995; pp 1-47.
19. For recent references, see: (c) Carreño, M. C.; García-Cerrada, S.; Urbano, A. Chem. Eur. J. 2003, 9, 4118-4131.
20. (d) Carreño, M. C.; García-Cerrada, S.; Sanz-Cuesta, M. J.; Urbano, A. J. Org. Chem. 2003, 68, 4315-4321.
21. (e) Carreño, M. C.; Ribagorda, M.; Somoza, A.; Urbano, A. Angew. Chem., Int. Ed. 2002, 41, 2755-2757.
22. (f) Carreño, M. C.; Ribagorda, M.; Posner, G. H. Angew. Chem., Int. Ed. 2002, 41, 2753-2755.
23. (g) Obringer, M.; Colobert, F.; Neugnot, B.; Solladié, G. Org. Lett. 2003, 5, 629-632.
24. (h) Hanquet, G.; Salom-Roig, X. J.; Lemeitour, S.; Solladié, G. Eur. J. Org. Chem. 2002, 2112.
25. Carreño, M. C.; García Ruano, J. L.; Martín, A.; Pedregal, C,; Rodrig-uez, J. H.; Rubio, A.; Sánchez, J.; Solladié, G. J. Org. Chem. 1990, 55, 2120-2128.
26. Colobert, F.; Des Mazery, R.; Solladié, G.; Carreño M. C. Org. Lett. 2002, 4, 1723-1725.
27. (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44-47.
28. (b) Maurer, B.; Thommen, W. Helv. Chim. Acta 1979, 62, 1096-1097.
29. (c) Van Dorp, D. A.; Ward, J. P. Experientia 1981, 37, 917-921.
30. For recent synthetic applications of β-ketosulfoxides, see: (a) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Garcia Ruano, J. L.; Solladié, G. J. Org. Chem. 1998, 63, 8918-8920.
31. (b) Solladié, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem, 2000, 2, 357-364.
32. (a) Mentzel, M.; Hoffmann, H. M. R. J. Prakt. Chem. 1997, 6, 517-524.
33. (b) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993.
34. (c) Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171-4174.
35. Solladié, G.; Hutt, J.; Girardin, A. Synthesis 1987, 173-175.
36. Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreño, M. C.; García-Ruano, J. L. J. Org. Chem. 1991, 56, 2317-2322.
37. García Ruano, J. L.; Fuerte, A.; Maestro, M. C. Tetrahedron: Asymmetry 1994, 5, 1443-1446.
38. Solladié, G.; Huser, N.; García Ruano, J. L.; Adrio, J.; Carreño, M. C.; Tito, A. Tetrahedron Lett. 1994, 35, 5297-5300.
39. (a) Solladié, G.; Demailly, G.; Greck, C. Tetrahedron Lett. 1985, 26, 435-438.
40. (b) Solladié, G.; Demailly, Greck, C. J. Org. Chem. 1985, 50, 1552-1554.
41. (c) Solladié, G.; Frechou, C.; Demailly, G.; Greck, C. J. Org. Chem. 1986, 51, 1912-1914.
42. (d) Solladié-Cavallo, A.; Suffert, J.; Adib, A.; Solladié, G. Tetrahedron Lett. 1990, 31, 6649-6652.
43. (e) Solladié, G.; Rubio, A.; Carreño M. C.; García-Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187-198.
44. Boukouvalas, J.; Fortier, G.; Radu, I. I. J. Org. Chem. 1998, 63, 916-917.
45. (a) Pothier, N.; Goldstein, S.; Deslongchamps, P. Helv. Chim. Acta 1992, 604-620.
46. (b) Chen, J.; Fletcher, M. T.; Kitching, W. Tetrahedron: Asymmetry 1995, 6, 967-972.
47. (c) White, J. D.; Bolton, G. L.; Dantanarayana, A. P.; Fox, C. M. J.; Hiner, R. N.; Jackson, R. W.; Sakuma, K.; Warrier, U. S. J. Am. Chem. Soc. 1995, 117, 1908-1939.
48. Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charrette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354-2359.
49. Pilli, R. A.; Rialto, V. B. Tetrahedron Asymmetry 2000, 11, 3675-3686.
50. Sugihara, H.; Tanikaga, R.; Kaji, A. Synthesis 1978, 881.
51. Cook, M. M.; Djerassi, C. J. Am. Chem. Soc. 1973, 95, 3678-3686.
52. Homma, K.; Mukaiyama, T. Chem. Lett. 1989, 259-262.
53. (a) De Albuquerque, I. L.; Galeffi, C.; Casinovi, C. G.; Marini-Bettolo, G. B. Gazz. Chim. Ital. 1964, 287-295.
54. (b) Galeffi, C.; Casinovi, C. G.; Marini-Bettòlo, G. B. Gazz. Chim. Ital. 1965, 95-100.
55. (c) Aragao Craveiro, A.; da Costa Prado, A.; Gottlieb, O. R.; Welerson de Albuquerque, P. C. Phytochemistry 1970, 9, 1869-1875.
56. Alcantara, A. F. de C.; Souza, M. R.; Piló-Veloso, D. Fitoterapia 2000, 71, 613-615
57. Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett. 2002, 4, 3919-3922.
58. Whalley, J. L.; Oldfield, M. F.; Botting, N. P. Tetrahedron 2000, 56, 455-460.
59. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 863-927.
60. Brewster, J. H. J. Am. Chem. Soc. 1959, 81, 5481-5493.
61. (a) Banwell, M. G.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1 1996, 967-969.
62. (b) Muraoka, O.; Okumura, M.; Maeda, T.; Wang, L.; Tanabe, G. Chem. Pharm. Bull. 1995, 43, 517-519.
63. (c) Varelis, P.; Graham, A. J.; Johnson, B. L.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1994, 47, 1735-1739.
64. (d) Lee, E., Jin, S., Lee, C. Tetrahedron Lett. 1993, 34, 4831-4834.
65. (e) Ishihara, K.; Mori, A.; Yamamoto, H. Tetrahedron 1990, 46, 4595-4612.
66. (f) Homma, K.; Mukaiyama, T. Chem. Lett. 1989, 893-896.
67. (g) Kobayashi, K.; Suginome, H. Bull. Chem. Soc. Jpn. 1989, 62, 951-952.
68. (h) Ishihara, K.; Mori, A.; Yamamoto, H. Tetrahedron Lett. 1987, 28, 6613-6616.
69. (i) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911-913.
70. (j) Nussbaumer, C.; Frater, G. Helv. Chim. Acta 1987, 70, 396-401.
71. (k) Gallagher, T. J. Chem. Soc., Chem. Commun. 1984, 1554-1555.
72. (l) Ley, S.; Lygo, B.; Molines, H. J. Chem. Soc., Perkin Trans. 1 1984, 2403-2405.
73. (m) Bates, H. A.; Deng, P. J. Org. Chem. 1983, 48, 4479-4481.
74. (n) Ley, S.; Lygo, B.; Molines, H.; Morton, J. A. J. Chem. Soc., Chem. Commun. 1982, 1521-1522.
75. (o) Kim, Y.; Mundy, B. P. J. Org. Chem. 1982, 47, 3556-3557.
76. (+)-Enantiomer: (a) Dixon, D. J.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans. 1 2000, 2385-2394.
77. (b) Banwell, M. G.; Bissett, B. D.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W. Aust. J. Chem. 1998, 51, 9-18.
78. (c) Edmunds, A. J. F.; Trueb, W. Tetrahedron Lett. 1997, 38, 1009-1012.
79. (d) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. J. Org. Chem. 1996, 61, 7309-7315.
80. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84-86.
81. (f) Mandai, T.; Ueda, M.; Kashiwagi, K.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1993, 34, 111-114.
82. (g) Bredenkamp, M. W.; Holzapfel, C. W.; Toerien, F. Synth. Commun. 1992, 22, 2447-2457.
83. (h) Hansson, S.; Miller, J. F.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 9660-9661.
84. (i) Greenspoon, N.; Keinan, E. J. Org. Chem. 1988, 53, 3723-3731.
85. (j) Jones, J. B.; Hinks, R. S. Can. J. Chem. 1987, 65, 704-707.
86. (k) Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474-3480.
87. (l) Semmelhack, M. F.; Bodurow, C. J. Am. Chem. Soc. 1984, 106, 1496-1498.
88. (m) Masaki, Y.; Serizawa, Y.; Nagata, K.; Kaji, K. Chem. Lett. 1983, 1601-1602.
89. (n) Seebach, D.; Pohmakotr, M.; Schregenberger, C.; Weidmann, B,; Mali, R. S.; Pohmakotr, S. Helv. Chim. Acta 1982, 65, 419-450.
90. (-)-Enantiomer: see ref 31c,f,g,h and the following: (o) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768-5774.
91. (p) Kotsuki, H.; Ushio, Y.; Kadota, I.; Ochi, M. Chem. Lett. 1988, 927-930.