Asymmetric Catalytic Friedel-Crafts Reaction of Silyl Enol Ethers with Fluoral: A Possible Mechanism of the Mukaiyama-aldol Reactions

Organic Letters

Volumn 1, Issue 12, 1999, Pages 2013-2016

  Ishii, Akihiro ^a,b   Kojima, Jun ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b CENTRAL GLASS CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001041017     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990330s     Document Type: Article

References (54)

1. Reviews: (a) Mukaiyama, T. Org. React. 1982, 28, 203.
2. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics in Stereochemistry; Interscience: New York, 1982; Vol. 13.
3. (c) Heathcock, C. H. Asymmetric Synthesis; Morrison, J. E., Ed.; Academic Press: New York, 1984; Vol. 3.
4. (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
5. (b) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137.
6. (c) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
7. Reviews: (a) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 1994; pp 1313.
8. (b) Heaney, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 733.
9. (c) Roberts, R. M.; Khalaf, A. A. In Friedel-Crafts Alkylation Chemistry. A Century of Discovery; Dekker: New York, 1984.
10. (d) Olah, G. A. Friedel-Crafts Chemistry; Wiley-Interscience: New York, 1973.
11. Chiral syn- or anti-α,β-dihydroxy thioesters as α-protected forms: (a) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994, 116, 9805.
12. (b) Mukaiyama, T.; Shiina, I.; Uchiro, H.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1994, 67, 1708. Chiral α-amino-β-hydroxy esters:
13. (c) Ito, Y.; Sawamura, M; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
14. (d) Ito, Y.; Sawamura, M; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron 1988, 44, 5253.
15. The recent mechanistic works of this reaction: (a) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
16. (b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323.
17. (c) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327.
18. (d) Denmark, S. E.; Henke, R. B. J. Am. Chem. Soc. 1991, 113, 2177.
19. (e) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039.
20. (f) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077.
21. (g) Bernardi, A.; Capelli, A. M.; Gennari, C.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1990, 55, 3576.
22. (h) Li, Y.; Paddon-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481.
23. In particular, asymmetric catalysis of carbon-carbon bond-forming reactions is the most attractive method. (a) Review: Iseki, K. Tetrahedron 1998, 54, 13887.
24. (b) Mikami, K.; Yajima, T.; Takasaki, T.; Matsukawa, S.; Terada, M.; Uchimaru, T.; Maruta, M. Tetrahedron 1996, 52, 85.
25. (c) Mikami, K.; Yajima, T.; Terada, M.; Uchimaru, T. Tetrahedron Lett. 1993, 34, 7591.
26. (d) Soloshonok, V. A.; Hayashi, T. Tetrahedron Lett. 1994, 35, 2713 and references therein.
27. Reviews: (a) Resnati, G.; Soloshonok, V. A., Eds. Tetrahedron 1996, 52, 1.
28. (b) Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992.
29. Reviews: (a) Soloshonok, V. A., Ed. Enantiocontrolled Synthesis of Fluoro-organic Compounds; John Wiley & Sons: Chichester, 1999.
30. (b) Ojima, I., McCarthy, J. R., Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; American Chemical Society: Washington, D.C., 1996.
31. (c) Resnati, G. Tetrahedron 1993, 49, 9385.
32. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812.
33. R = 19 min (2R,3S), 37 min (2S,3R).
34. The F - C products were not obtained in the reaction of aliphatic ketone-derived silyl enol ethers without aromatic substituents such as 1-tert-butyldimethylsilyloxy-1-cyclohexene and 2-tert-butyldimethylsilyloxy-1-heptene.
35. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. See ref 1b.
36. 3) of 3a (vinylic proton, 5.08 ppm (major), 5.15 ppm (minor); allylic proton, 4.46 ppm (major), 4.98 ppm (minor)): Rummens, F. H. A.; de Haan, J. W. Org. Magn. Res. 1970, 2, 351.
37. R = positive.
38. (a) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W.; Goodman, S. N. Tetrahedron Lett 1997, 37, 6513.
39. (b) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940.
40. (b) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940.
41. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
42. (a) Schwesinger, R.; Willaredt, J. In Houben-Weyl E21; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 8.
43. (b) Sharpless proposed the formation of hydrogen bond between hydroxy groups and m-CPBA: Sharpless, K. B.; Verhoeven, T. R. Aldrichimca Acta 1979, 12, 63.
44. (c) Berti, G. In Topics of Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, L 1973; Vol. 7, pp 141, 147.
45. (d) Vedejs, E.; Dent, W. H. J. Am. Chem. Soc. 1989, 111, 6861.
46. (e) Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1862.
47. (f) Mihelich, E. D. Tetrahedron Lett. 1979, 20, 4729.
48. (g) Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 20, 4733.
49. (h) Chautemps, P.; Pierre, J.-L. Tetrahedron 1976, 32, 549.
50. (i) Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc. B 1970, 1374.
51. 3) of 5 (syn 23.4 ppm, anti 25.1 ppm): Heathcock, C. H.; Pirrung M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294.
52. max = 55.0°) were used for the solution of the structure. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included but not refined. R = 0.042, Rw = 0.156. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-133938. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB@ 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk). We are grateful to Dr. Masahiro Terada for his useful discussion and technical support on the X-ray analysis.
53. R = 16 min (syn), 37 min (anti)).
54. 3) of 4d (syn 11.9 ppm, anti 16.3 ppm), 4e (anti 16.5 ppm), respectively. See ref 18.