Synthesis, equilibration, and coupling of 4-lithio-1,3-dioxanes: Synthons for syn- and anti-1,3-diols

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6849-6860

  Rychnovsky, Scott D ^a   Buckmelter, Alexandre J ^a   Dahanukar, Vilas H ^a   Skalitzky, Donald J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE; LITHIUM DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; KINETICS; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032888368     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909352     Document Type: Article

References (71)

1. (a) Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481-7.
2. (b) Still, W. C.; Sreekumar, C. J. Am. Chem. Soc. 1980, 102, 1201-2.
3. (a) Chan, P. C.-M.; Chong, J. M. J. Org. Chem. 1988, 53, 5584-6.
4. (b) Chong, J. M.; Mar, E. K. Tetrahedron Lett. 1990, 31, 1981-4.
5. (c) Chan, P. C. M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1985-8.
6. (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283-316.
7. (b) Hoppe, D.; Ahrens, H.; Guarnieri, W.; Helmke, H.; Kolczewski, S. Pure Appl. Chem. 1996, 68, 613-8.
8. (c) Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1994, 66, 1479-86.
9. (d) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-60.
10. (a) Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064-71.
11. (b) Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1979, 43, 1064-71.
12. Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152-61.
13. (a) Cohen, T.; Matz, J. R. Synth. Commun. 1980, 10, 311-7.
14. (b) Cohen, T.; Lin, M. T. J. Am. Chem. Soc. 1984, 106, 1130-1.
15. (c) Boeckman, R. K.; Enholm, E. J.; Demko, D. M.; Charette, A. B. J. Org. Chem. 1986, 51, 4743-5.
16. (a) Rychnovsky, S. D. J. Org. Chem. 1989, 54, 4982-4.
17. (b) Rychnovsky, S. D.; Mickus, D. E. Tetrahedron Lett. 1989, 30, 3011-4.
18. Rychnovsky, S. D.; Powers, J. P.; Lepage, T. J. J. Am. Chem. Soc. 1992, 114, 8375-84.
19. Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924-30.
20. (a) Saunders: R. H.; Murray, M. J.; Cleveland, F. F. J. Am. Chem. Soc. 1943, 65, 1714-7.
21. (b) Spath, E.; Lorenz, R.; Fruend, E. Chem. Ber. 1943, 76, 1196-208.
22. (c) Alexander, E. R.; Marvell, E. N. J. Am. Chem. Soc. 1950, 72, 1396.
23. (d) Hine, J.; Houston, J. G.; Jensen, J. H. J. Org. Chem. 1965, 30, 1184-8.
24. (e) Andersson, R.; Theander, O.; Westerlund, E. Carbohydr. Res. 1978, 61, 501-9.
25. (f) Duke, C. C.; MacLeod, J. K.; Williams, J. F. Carbohydr. Res. 1981, 95, 1-26.
26. (g) Cloux, R.; Schlosser, M. Helv. Chim. Acta 1984, 67, 1470-4.
27. Rychnovsky, S. D.; Skalitzky, D. J. J. Org. Chem. 1992, 57, 4336-9.
28. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-9.
29. Jung, M. E.; D'amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208-9.
30. Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-20.
31. (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71-4.
32. (b) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1997, 35, 2708-48.
33. Pettit, G. R.; Herald, C. L.; Doubek, D. L.; Herald, D. L. J Am Chem. Soc. 1982, 104, 6846-8.
34. Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392-8.
35. NOE data for compounds 28, 32, 27c, and 25c are included in the Supporting Information, as is the preparation of 31.
36. (a) Sawyer, J. S.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1984, 106, 3376-7.
37. (b) Sawyer, J. S.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842-53.
38. (a) Linderman, R. J.; Godfrey, A. Tetrahedron Lett. 1986, 27, 4553-6.
39. (b) Hutchinson, D. K.; Fuchs, P. L. J. Am. Chem. Soc. 1987, 109, 4930-9.
40. (c) Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1990, 55, 5428-30.
41. (d) Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1991, 56, 5491-3.
42. (c) Prandi, J.; Audin, C.; Beau, J.-M. Tetrahedron Lett. 1991, 32, 769-72.
43. (a) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2.
44. (b) Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791-3.
45. (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-88.
46. McGarvey, G. J.; Kimura, M. J. Org. Chem. 1982, 47, 5420-2.
47. Yamada, J.-I.; Abe, H.; Yamamoto, Y. J. Am. Chem, Soc. 1990, 112, 6118-20.
48. Linderman, R. J.; McKenzie, J. R. Tetrahedron Lett. 1988, 29, 3911-4.
49. (a) Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368-70.
50. (b) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6019-22.
51. (c) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-50.
52. The X-ray structure of 37 is illustrated in the Supporting Information. We thank Dr. Joseph Ziller from the University of California, Irvine, Department of Chemistry for determining the X-ray structure.
53. Rychnovsky, S. D.; Sinz, C. J. Tetrahedron Lett. 1998, 39, 6811-4.
54. Configurational assignments for compounds 39 and 40 are described in the Supporting Information.
55. Lehn, J.-M.; Wipff, G. J. Am. Chem. Soc. 1976, 98, 7498-7505.
56. Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301-12.
57. The pseudo-A value for methyl at the C2 position of a 1,3-dioxane is >3.55 kcal/mcl, and this does not begin to account for the 1,3-diaxial interaction in the cis-2,4-dimethyl-1,3-dioxane. Eliel, E. L.; Knoeber, M. C. J. Am. Chem. Soc. 1988, 90, 3444-58.
58. The coordinates for each calculated structure in Figures 1 and 2 are included in the Supporting Information.
59. For the 2,6-dimethyl series, seven cis and seven trans conformera were evaluated at HF/3-21G and led to three unique cis and five unique trans conformers. In the 5-equatorial 2,5,6-trimethyl series, eight cis and eight trans conformers were evaluated at HF/3-21G and led to four unique cis and six unique trans conformers. Finally, in the 5-axial 2,5,6-trimethyl series, six cis and six trans conformers were evaluated at HF/3-21G and led to three unique cis and five unique trans conformers.
60. On an absolute scale, the 4,6-cis 5-axial conformation is 1.81 kcal/mol higher than the 4,6-cis 5-equatorial isomer. This difference is about twice the expected pseudo-A value (0.80-0.97 kcal/mol) for methyl at the C5 position of a 1,3-dioxane (ref 31). Steric interactions between the equatorial C4 lithium atom and the adjacent axial C5 methyl group may account for the difference.
61. Buckmelter, A. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1998, 120, 5589-90.
62. Mohamadi, P.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-67.
63. Rotamers around the C4-S and S-Ph bonds lead to a group of structures with similar steric energies for each ring conformation. Rotations around these bonds should have little effect on the chemistry and were ignored in the analysis.
64. (a) Malatesta, V.; McKelvey, R. D.; Babcock, B. W.; Ingold, K. U. J. Org. Chem. 1979, 44, 1872-3.
65. (b) Gregory, A. R.; Malatesta, V. J. Org. Chem. 1980, 45, 122-5.
66. (a) Whitesides, G. M.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 4878-88.
67. (b) Fraenkel, G.; Cottrell, C. E.; Dix, D. T. J. Am. Chem. Soc. 1971, 93, 1704-8.
68. Reich, H. J.; Medina, M. A.; Bowe, M. D. J. Am. Chem. Soc. 1992, 114, 11003-4.
69. The general experimental is included in the Supporting Information.
70. Gage, J. R.; Evans, D. A. Organic Syntheses; Wiley: New York, 1993; Coll. Vol. VIII, pp 339-343.
71. Mudryk, B.; Cohen, T. Org. Synth. 1993, 72, 173-179.