Enantio- and diastereoselective synthesis of cyclic β-hydroxy allylsilanes via sequential aldehyde γ-silylallylboration and ring-closing metathesis reactions

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1693-1696

  Heo, Jung Nyoung ^a   Micalizio, Glenn C ^a   Roush, William R ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORIC ACID; SILANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ALDEHYDES; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; SILANES; STEREOISOMERISM;

EID: 0041517640     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034347t     Document Type: Article

References (44)

1. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063, and references cited therein.
2. For review, see: Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
3. (a) Panek, J. A.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868.
4. (b) Panek, J. A.; Beresis, R. J. Org. Chem. 1993, 58, 809.
5. (a) Akiyama, T.; Sugano, M.; Kagoshima, H. Tetrahedron Lett. 2001, 42, 3889.
6. (b) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885.
7. (c) Angle, S. R.; El-Said, N. A. J. Am. Chem. Soc. 2002, 124, 3608.
8. (a) Roberson, C. W.; Woerpel. K. A. J. Am. Chem. Soc. 2002, 124, 11342.
9. (b) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2001, 3, 675.
10. (c) Roberson, C. W.; Woerpel, K. A. Org. Lett. 2000, 2, 621.
11. (d) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2000, 2, 1379.
12. (e) Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434.
13. (a) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461.
14. (b) Micalizio, G. C.; Roush, W. R. Org. Lett. 2001, 3, 1949.
15. (a) Elliot, M. C.; Williams, E. J. Chem. Soc., Perkin Trans. 1 2001, 2303.
16. (b) Elliot, M. C. J. Chem. Soc., Perkin Trans. 1 2000, 1291.
17. Roush, W. R.; Pinchuk, A. N.; Micalizio, G. C. Tetrahedron Lett. 2000, 41, 9413.
18. (a) Fleming, I.; Higgins, D.; Lawrence, N. J.; Thomas, A. P. J. Chem. Soc., Perkin Trans. 1 1992, 3331.
19. (b) Landais, Y.; Zekri, E. Tetrahedron Lett. 2001, 42, 6547.
20. Roush, W. R.; Grover, P. T. Tetrahedron 1992, 48, 1981.
21. For reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
22. For reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
23. For olefin metathesis reactions of allylsilanes: (a) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (b) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209. (c) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964.
24. For olefin metathesis reactions of allylsilanes: (a) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (b) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209. (c) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964.
25. For olefin metathesis reactions of allylsilanes: (a) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (b) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209. (c) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964.
26. Enantioselectivity (% ee) of this reaction was determined by Mosher ester analysis: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
27. Prepared by the improved literature method: Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (b) For the original report: Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
28. Prepared by the improved literature method: Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (b) For the original report: Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
29. Crimmins, M. T.; Kirincich, S. J.; Wells, A. J.; Choy, A. L. Synth. Commun. 1998, 28, 3675.
30. For trans isomers, see ref 9b and: Clive, D. L. J.; Zhang, C.; Zhou, Y.; Tao, Y. J. Organomet. Chem. 1995, 489, C35.
31. (a) Gu, Y. G.; Wang, K. K. Tetrahedron Lett. 1991, 32, 3029.
32. (b) Wang, K. K.; Gu, Y. G.; Liu, C. J. Am. Chem. Soc. 1990, 112, 4424.
33. Danheiser, R. L.; Carini, D. J.; Fink, D. M.; Basak, A. Tetrahedron 1983, 39, 935.
34. Brown, H. C.; Joshi, N. N. J. Org. Chem. 1988, 53, 4059.
35. (a) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1985, 107, 2564.
36. (b) Roush, W. R. In Comprehensive Organic Synthesis; Heathcock, C., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1.
37. (a) Hudrlik, P. F.; Peterson, D. J. Am. Chem. Soc. 1975, 97, 1464.
38. (b) Koreeda, M.; Ciufolini, M. A. J. Am. Chem. Soc. 1982, 104, 2308.
39. For synthesis of 13, see Supporting Information
40. (a) Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
41. (b) Lin, N.-H.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9062.
42. Cyclohexenylsilanes deriving from 15c and 16c were also obtained (5-8% yield) but are not shown in Scheme 3.
43. 2) for this reaction failed to give [3 + 2]-annulation products, 20 or 21.
44. Heo, J.-N.; Holson, E. B.; Roush, W. R. Org. Lett. 2003, 5, 1697.