Anti-1,3-diols by addition of dialkylzinc reagents to 4-acetoxy-1,3- dioxanes

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 2026-2037

  Powell, Noel A ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 ACETOXY 1,3 DIOXANE; DIOXANE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; MOLECULAR INTERACTION; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0033582985     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982264y     Document Type: Article

References (81)

1. (a) Macrolide Antibiotics: Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: New York, 1984.
2. (b) Rychnovsky, S. D. Chem. Rev. 1985, 95, 2021-2040.
3. (a) Rychnovsky, S. D.; Griesgraber, G.; Kim, J. J. Am. Chem. Soc. 1994, 116, 2621-2622.
4. (b) Rychnovsky, S. D.; Khire, E. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058-2059.
5. (a) Rychnovsky, S. D.; Rodriguez, C. J. Org. Chem. 1992, 57, 4793-4795.
6. (b) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-65.
7. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635-645.
8. (b) Schneider, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 1375-1378.
9. (a) Rychnovsky, S. D.; Griesgraber, G.; Zeller, S.; Skalitzky, D. J. J. Org. Chem. 1990, 56, 5161-5169.
10. (b) Rychnovsky, S. D.; Plzak, K.; Pickering, D. Tetrahedron Lett. 1994, 35, 6799-6802.
11. (c) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022-3023.
12. (a) Rychnovsky, S. D.; Zeller, S.; Skalitzky, D. J.; Griesgraber, G. J. Org. Chem. 1990, 55, 5550-5551.
13. (b) Rychnovsky, S. D.; Griesgraber, G. J. Org. Chem. 1992, 57, 1559-1563.
14. (c) Rychnovsky, S. D.; Rodriguez, C. J. Org. Chem. 1992, 57, 4793-4795.
15. (d) Rychnovsky, S. D.; Swenson, S. S. J. Org. Chem. 1997, 82, 1333-1340.
16. Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320.
17. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982,104, 4976-4978.
18. For related 1,3-diol synthons see Davis, A. P.; Hegarty, S. C. J. Am. Chem. Soc. 1992, 114, 2745-2746.
19. Rychnovsky, S. D.; Skalitzky, D. J. J. Org. Chem. 1992, 57, 4336-4339.
20. Rychnovsky, S. D.; Skalitzky, D. J. Synlett 1995, 555-556.
21. Boons, G.-J.; Eveson, R.; Smith, S.; Stauch, T. Synlett 1996, 536-538.
22. Rychnovsky, S. D.; Sinz, C. J. Tetrahedron Lett. 1998, 39, 6811-6814.
23. Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1998, 39, 3103-3106.
24. Rychnovsky, S. D.; Powell, N. A. J. Org. Chem. 1997, 62, 6460-6461.
25. Rychnovsky, S. D.; Dahanukar, V.; Buckmelter, A., manuscript in preparation.
26. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858.
27. (a) Schreiber, S. L.; Reagna, J. Tetrahedron Lett. 1986, 27, 2945-2948.
28. (b) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448-463.
29. (c) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841.
30. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
31. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188.
32. Reviews: (a) Solladie, G. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; vol. 2A, Chapter 6.
33. (b) Evans, D. A. Science 288, 240, 420.
34. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
35. (d) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
36. (a) Nützel, K. In Methoden der Organischen Chemie (Houben-Weyl); G. Theime: Stuttgart, 1973; Vol. 13/2a, p 553.
37. (b) Frankland, E. Liebigs Ann. Chem. 1865, 95, 28; 1859, 111, 44.
38. (b) Frankland, E. Liebigs Ann. Chem. 1865, 95, 28; 1859, 111, 44.
39. (c) Noller, C. R. Organic Syntheses; Wiley: New York, 1943; Coll. Vol. II, p 184.
40. (d) Sorroos, H.; Morgana, M. J. Am. Chem. Soc. 1944, 66, 893.
41. Reviews: (a) Knochel, P. Synlett 1995, 393-402.
42. (b) Knochel, P. Chemtracts-Org. Chem. 1995, 205-221.
43. (a) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008-1009.
44. (b) Bussche-Hünnefeld, J. L.; Seebach, D Tetrahedron 1992, 48, 5719-5730.
45. (c) Weber, B.; Seebach, D Tetrahedron 1994, 50, 7473-7484.
46. (a) Rozema, M. J.; Sidduri, A.; Knochel, P. J. Org. Chem. 1992, 57, 1956-1958.
47. (b) Rozema, M. J.; Eisenbur, C.; Lütjens, H.; Ostwald, R.; Belyk, K.; Knochel, P. Tetrahedron Lett. 1993, 34, 3115-3118.
48. Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 20, 5114-5115.
49. (a) Langer, F.; Waas, J.; Knochel, P. Tetrahedron Lett. 1993, 34, 5261-5264.
50. (b) Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229-8243.
51. Vettle, S.; Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 1023-1026.
52. (a) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197-5200.
53. (b) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853-12910.
54. (a) Kozikowshi, A. P.; Konoike, T.; Ritter, A. Carbohydrate Res. 1987, 171, 109-124,
55. (b) Tomooka, K.; Matsuzawa, K.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6339-6342.
56. (c) Thorn, S. N.; Gallagher, T. Synlett 1996, 185-187.
57. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-860.
58. Aponick, A.; McKinley, J. D.; Raber, J. C.; Wigal, C. T. J. Org. Chem. 1998, 63, 2676-2678.
59. (a) Demuth, M.; Mikhail, G. Synthesis 1982, 827-828.
60. (b) Demuth, M.; Mikhail, G. Tetrahedron 1983, 39, 991-997.
61. An alternative pathway was suggested by one of the referees, namely that the reaction of 7 could give 5 initially, followed by subsequent isomerization to 4. Two arguments detract from this possibility. First, it would require very selective equatorial addition of diethylzinc to 9, which appears unlikely considering the high axial selectivity observed throughout this work. Second, the isomerization of 5 to 4 would need to account for the observed 5:94 ratio, where the expected equilibrium ratio is 50:50. The alternative pathway thus requires a contra-thermodynamic equilibration and cannot account for the bulk of the product.
62. Rathke, M. W.; Yu, H. J. Org. Chem. 1972, 37, 1732-1734.
63. (a) Micouin, L.; Oestreich, M.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997,36,245-246,
64. (b) Micouin, L.; Knochel, P. Synlett 1997, 327-328.
65. (c) Darcel, C.; Flachsmann, F.; Knochel, P. Chem. Commun. 1998, 205-206.
66. (a) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651-2652.
67. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995,60, 1081-1083.
68. Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114, 2592-2602.
69. Details for the synthesis and characterization of 22a-c are given in the Supporting Information
70. Crich, D.; Sun, S. J. Am. Chem. Soc. 1997, 119, 11217-11223.
71. Berninger, J.; Koert, U.; Eisenberg-Höhl, C.; Knochel, P. Chem. Ber. 1995, 128, 1021-1028.
72. Syntheses of 34-36 are described in Powell, N. A., Ph.D. Thesis, University of California, Irvine, 1998. The preparation of these compounds will be discussed in a forthcoming paper by S. D. Rychnovsky, V. H. Dahanukar, A. J. Buckmelter, and D. S. Skalitzky.
73. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley & Sons: New York, 1991; pp 118-135.
74. (a) Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1565-1567.
75. (b) Deslongchamps, P.; Moreau, C. Can. J. Chem. 1971, 49, 2465-2467.
76. (c) Deslongchamps, P.; Atlani, P.; Fréhel, D.; Malaval, A.; Moreau, C. Can. J. Chem. 1974, 52, 3651-3664.
77. Nouguier, R. Tetrahedron Lett. 1982, 23, 2951-2. Pegg, N. A.; Paquette, L. A. J. Org. Chem. 1991, 56, 2461-8.
78. Nouguier, R. Tetrahedron Lett. 1982, 23, 2951-2. Pegg, N. A.; Paquette, L. A. J. Org. Chem. 1991, 56, 2461-8.
79. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley &Sons: New York, 1991.
80. (b) Kocienski, P. J. Protecting Groups; Thieme: New York, 1994.
81. Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlelt 1996, 839-841.