Tandem intramolecular silylformylation-allylsilylation [15]

Journal of the American Chemical Society

Volumn 122, Issue 35, 2000, Pages 8587-8588

  Zacuto, Michael J ^a   Leighton, James L ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; NATURAL PRODUCT; SILANE DERIVATIVE;

CHEMICAL REACTION; LETTER; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0033828571     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002425r     Document Type: Letter

References (30)

1. Rychnovsky, S. D. Chem. Rev. 1995, 95, 2012-2040.
2. (a) Leighton, J. L.; O'Neil, D. N. J. Am. Chem. Soc. 1997, 119, 11118-11119.
3. (b) Leighton, J. L.; Chapman, E. J. Am. Chem. Soc. 1997, 119, 12416-12417.
4. (c) Sarraf, S. T.; Leighton, J. L. Tetrahedron Lett. 1998, 39, 6423-6426.
5. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 403-405.
6. For reviews of other approaches, see ref 1 and the following: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635-645. (b) Schneider, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 1375-1378.
7. For reviews of other approaches, see ref 1 and the following: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635-645. (b) Schneider, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 1375-1378.
8. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
9. For a review on the Tamao and Fleming oxidations, see: Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
10. 3, followed by 2 equiv of allyl-MgBr. This reaction provides the desired diallylsilyl ethers in 50-90% yields, with more sterically hindered alcohols giving better results. See the Supporting Information for details.
11. Stereochemical determinations were made using the method of Rychnovsky: Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515. See the Supporting Information for details.
12. Reetz, M. T.; Jung, A.; Bolm, C. Tetrahedron 1988, 44, 3889-3898.
13. Uyeo, S.; Itani, H. Tetrahedron Lett. 1991, 32, 2143-2146.
14. Linderman, R. J.; Chen, K. J. Org. Chem. 1996, 67, 2441-2453.
15. Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59, 7152-7155.
16. (a) Myers, A. G.; Kephart, S. E.; Chen, H. J. Am. Chem. Soc. 1992, 114, 7922-7923.
17. For another example of an uncatalyzed silicon-mediated aldol reaction, see: (b) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 112, 9672-9674.
18. (c) Myers, A. G.; Widdowson, K. L.; Kukkola, P. J. Am. Chem. Soc. 1992, 114, 2765-2767.
19. (a) Denmark, S. E.; Griedel, B, D.; Coe, D. M. J. Org. Chem. 1993, 58, 988-990.
20. (b) Denmark, S. E.; Griedel, B, D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026-7043.
21. Denmark, S. E.; Jacobs, R. T.; Dai-Ho, G.; Wilson, S. Organometallics 1990, 9, 3015-3019.
22. Several relevant X-ray structures have been reported. See, for example: Shaw, J. T.; Woerpel, K. A. J. Org. Chem. 1997, 62, 6706-6707.
23. Hoveyda has reported relevant observations regarding the Lewis acidity of oxasilacyclopentanes of this type. See: Young, D. G. J.; Hale, M. R.; Hoveyda, A. H. Tetrahedron Lett. 1996, 37, 827-830.
24. (a) Tamao, K.; Tanaka, T.; Nakajima, T.; Sumiya, R.; Arai, H.; Ito, Y. Tetrahedron Lett. 1986, 27, 3377-3380.
25. (b) Tamao, K.; Nakajima, T.; Sumiya, R.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1986, 108, 6090-6093.
26. These are the conditions employed by Utimoto. See ref 11.
27. We exclude a fifth possible tbp isomer, wherein the oxasilacyclopentane and the aldehyde O span only eqatorial positions, since it is expected to be highly strained.
28. Myers has elegantly established a mechanism involving pseudorotation for the uncatalyzed aldol reactions of O-silyl ketene N,O-acetals. See ref 12c.
29. For an excellent discussion of pseudorotation of pentacoordinate silicon and lead references, see: (a) Stevenson, W. H., III; Wilson, S.; Martin, J. C.; Farnham, W. B. J. Am. Chem. Soc. 1985, 107, 6340-6352. (b) Stevenson, W. H., III; Martin, J. C. J. Am. Chem. Soc. 1985, 107, 6352-6358.
30. For an excellent discussion of pseudorotation of pentacoordinate silicon and lead references, see: (a) Stevenson, W. H., III; Wilson, S.; Martin, J. C.; Farnham, W. B. J. Am. Chem. Soc. 1985, 107, 6340-6352. (b) Stevenson, W. H., III; Martin, J. C. J. Am. Chem. Soc. 1985, 107, 6352-6358.