Synthesis of Optically Pure Arylsilylcarbinols and Their Use as Chiral Auxiliaries in Oxacarbenium Ion Reactions

Journal of Organic Chemistry

Volumn 68, Issue 26, 2003, Pages 10135-10145

  Huckins, John R ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL REAGENTS; TURNOVER EFFICIENCY;

ALCOHOLS; ALDEHYDES; CATALYSTS; HYDROGENATION; KETONES; STEREOCHEMISTRY; UNSATURATED COMPOUNDS;

AROMATIC COMPOUNDS;

ALDEHYDE; ALLYLTRIMETHYLSILANE; CARBENOID; KETONE DERIVATIVE; METHANOL DERIVATIVE; OXACARBENIUM ION; SILYLCARBINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 0346362505     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035260o     Document Type: Article

References (59)

1. Sutherland, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 341-377.
2. (b) Johnson, W. S. Tetrahedron 1991, 47, R11-R50.
3. (c) Johnson, W. S. Angew. Chem. 1976, 88, 33-41.
4. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 527-561.
5. (b) Adams, D. R.; Bhatnagar, S. P. Synthesis 1977, 661-672.
6. For the purposes of this paper, the most important example is the addition of allyltrimethylsilane, the Hosomi-Sakurai reaction: Hosomi, A.; Endo, M.; Sakurai, H. Chem. Lett. 1976, 941-942.
7. (b) Sakurai, H. Pure Appl. Chem. 1982, 54, 1-22.
8. (b) For a review of the C-C bond formation with silyl Lewis acids, see: Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733-772.
9. (a) Imwinkelried, R.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1985, 24, 765-766.
10. (b) Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121-1124.
11. (c) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779-4782.
12. (d) Andrus, M. B.; Lepore, S. D. Tetrahedron Lett. 1995, 36, 9149-9152.
13. (e) Manju, K.; Trehan, S. Chem. Commun. 1999, 1929-1930.
14. (a) Tietze, L. F.; Dolle, A.; Schiemann, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1372-1373.
15. (b) Tietze, L. F.; Schiemann, K.; Wegner, C. J. Am. Chem. Soc. 1995, 117, 5851-5852.
16. (c) Tietze, L. F.; Wegner, C.; Wulff, C. Synlett 1996, 5, 471-472.
17. (d) Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem.-Eur. J. 1996, 2, 1164-1172.
18. (e) Tietze, L. F.; Wegner, C.; Wulff, C. Synlett 1996, 471.
19. (f) Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem.-Eur. J. 1998, 4, 1862-1869.
20. (g) Tietze, L. F.; Wegner, C.; Wulff, C. Eur. J. Org. Chem. 1998, 1639-1644.
21. (h) Tietze, L. F.; Weigand, B.; Volkel, L.; Wulff, C.; Bittner, C. Chem.-Eur. J. 2001, 7, 161-168.
22. For a review, see: Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477-511.
23. (b) Johnson, W. S.; Harbert, C. A.; Stipanovic, R. D. J. Am. Chem. Soc. 1968, 90, 5279-5280.
24. (c) Johnson, W. S.; Harbert, C. A.; Ratcliffe, B. E.; Stipanovic, R. D. J. Am. Chem. Soc. 1976, 98, 6188-6193.
25. (d) Bartlett, P. A.; Johnson, W. S.; Elliot, J. D. J. Am. Chem. Soc. 1983, 105, 2088-2089.
26. Linderman, R. J.; Anklekar, T. V. J. Org. Chem. 1992, 57, 5078-5080.
27. (b) Linderman, R. J.; Chen, K. J. Org. Chem. 1996, 61, 2441-2453.
28. (c) Linderman, R. J.; Chen, S. Tetrahedron Lett. 1996, 37, 3819-3822.
29. Cossrow, J.; Rychnovsky, S. D. Org. Lett. 2002, 4, 147-150.
30. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
31. (b) Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285-288.
32. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
33. Rychnovsky, S. D.; Cossrow, J. Org. Lett. 2003, 5, 2367-2370.
34. For example, see: Sinz, C. J.; Rychnovsky, S. D. Angew. Chem., Int. Ed. 2001, 40, 3224-3227.
35. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040.
36. Brook, A. G. J. Am. Chem. Soc. 1957, 79, 4373-4375.
37. (b) Olah, G. A.; Berrier, A. L.; Field, L. D.; Prakash, G. K. S. J. Am. Chem. Soc. 1982, 104, 1349-1355.
38. Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. M. J. Org. Chem. 1991, 56, 7076-7083.
39. (b) Soderquist, J. A.; Anderson, C. L.; Miranda, E. I.; Rivera, I.; Kabalka, G. W. Tetrahedron Lett. 1990, 31, 4677-4680.
40. Linderman, R. J.; Ghannam, A.; Badejo, I. J. Org. Chem. 1991, 56, 5213-5216.
41. Corey, E. J.; Bakshi, K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
42. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926.
43. (c) Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880-2888.
44. (d) Xavier, L. C.; Mohan, J. J.; Mathre, D. J.; Thompson, A. S.; Carroll, J. D.; Corley, E. G.; Desmond, R. Org. Synth. 1996, 74, 50-71.
45. The experimental details and characterization of new compounds are included in the Supporting Information.
46. All of the arylsilylcarbinols 12 and compound 1 showed negative optical rotations, and in each case the major enantiomer eluted first on a Chiracel OD-H column. These physical properties are consistent with the proposal that all of the reduction products share the S configuration.
47. Corey, E. J.; Seebach, D. J. Am. Chem. Soc. 1967, 89, 434-436.
48. Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanaski, S. W. J. Org. Chem. 1985, 50, 5393-5396.
49. Narasaka, K.; Morikawa, A.; Salgo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773-2776.
50. The R configuration of acylsilane 16 was assigned by Mosher's ester analysis. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
51. Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647-656.
52. A similar problem was found with a model of the phenylmethylcarbinol auxiliary, where the model did not predict the observed product. Broeker, J. L. ; Hoffmann, R. W.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5006-5017.
53. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
54. (b) Nguyen, T. A.; Eisenstein, O. Tetrahedron Lett. 1976, 155-158.
55. (c) Nguyen, T. A.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61-70.
56. (d) Ahn, N. T. Top. Curr. Chem. 1980, 88, 145-162.
57. Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998-10999.
58. (b) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997-3000.
59. (c) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1994, 116, 7915-7979.