Lewis acid-catalyzed addition of alkenylzirconocenes to carbonyl compounds: Remarkable activity of trimethylsilyl triflate

Synthesis

Volumn , Issue 10, 2004, Pages 1566-1572

  Murakami, Teiichi ^a   Furusawa, Kiyotaka ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Addition reactions; Alkenylation; Hydrozirconation; Lewis acids; Stereoselectivity

Indexed keywords

ACIDS; ALCOHOLS; CATALYSIS; CATALYST ACTIVITY; KETONES;

LEWIS ACIDS;

ADDITION REACTIONS;

CARBONYL DERIVATIVE; LEWIS ACID; SULFONIC ACID DERIVATIVE; TRIMETHYLSILYL TRIFLATE; UNCLASSIFIED DRUG; ZIRCONOCENE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; REACTION ANALYSIS;

EID: 3142776385     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829108     Document Type: Article

References (51)

1. (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, S.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
2. (b) For a review, see: Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299.
3. Murakami, T.; Furusawa, K. Tetrahedron 2002, 58, 9257.
4. (a) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
5. (b) For a review, see: Liang, X.; Andersch, J.; Bols, M. J. Chem Soc., Perkin Trans, 1 2001, 2136.
6. For reviews, see: (a) Labinger, J. A.In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 667-702. (b) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
7. For reviews, see: (a) Labinger, J. A.In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 667-702. (b) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
8. (a) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
9. (b) Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1992, 71, 77.
10. For a review, see: Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447.
11. (a) Sugiyama, T.; Sugawara, H.; Watanabe, M.; Yamashita, K. Agric. Biol. Chem. 1984, 48, 1841.
12. (b) Maruyama, T.; Sugiyama, T.; Yamashita, K. Agric. Biol. Chem. 1986, 50, 1923.
13. (c) For a review, see: Sugiyama, T. Nippon Nogeikagaku Kaishi 1990, 64, 191; Chem. Abstr. 1990, 113, 58095.
14. (c) For a review, see: Sugiyama, T. Nippon Nogeikagaku Kaishi 1990, 64, 191; Chem. Abstr. 1990, 113, 58095.
15. (a) Chattopadhyay, A.; Mamdapur, V. R. J. Org. Chem. 1995, 60, 585.
16. (b) Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104.
17. (c) Sharma, A.; Chattopadhyay, S. Tetrahedron: Asymmetry 1999, 10, 883.
18. (a) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725.
19. (b) For a review, see: Schmidt, R. R. Pure Appl. Chem. 1989, 61, 1257.
20. (a) Ohlsson, J.; Magnusson, G. Carbohydr. Res. 2001, 331, 91.
21. (b) Gargano, J. M.; Lees, W. J. Tetrahedron Lett. 2001, 42, 5845
22. . (c) Compostella, F.; Franchira, L.; Giovenzana, G. B.; Panza, L.; Prosperi, D.; Ronchetti, F. Tetrahedron: Asymmetry 2002, 13, 867.
23. (a) Maeta, H.; Hashimoto, T.; Hasegawa, T.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5965.
24. (b) Suzuki, K.; Hasegawa, T.; Imai, T.; Maeta, H.; Ohba, S. Tetrahedron 1995, 51, 4483.
25. Zheng, B.; Srebnik, M. J. Org. Chem. 1995, 60, 3278.
26. Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
27. Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521.
28. Yoshida, J.; Nakagawa, M.; Seki, H.; Hino, T. J. Chem. Soc., Perkin Trans, 1 1992, 343.
29. For selected references: (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843. (b) Mead, K.; MacDonald, T. L. J. Org. Chem. 1985, 50, 422. (c) For a review. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. (d) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 53-55. (e) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 108-111. (f) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 153-154. (g) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 339.
30. For selected references: (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843. (b) Mead, K.; MacDonald, T. L. J. Org. Chem. 1985, 50, 422. (c) For a review. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. (d) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 53-55. (e) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 108-111. (f) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 153-154. (g) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 339.
31. For selected references: (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843. (b) Mead, K.; MacDonald, T. L. J. Org. Chem. 1985, 50, 422. (c) For a review. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. (d) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 53-55. (e) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 108-111. (f) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 153-154. (g) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 339.
32. For selected references: (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843. (b) Mead, K.; MacDonald, T. L. J. Org. Chem. 1985, 50, 422. (c) For a review. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. (d) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 53-55. (e) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 108-111. (f) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 153-154. (g) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 339.
33. For selected references: (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843. (b) Mead, K.; MacDonald, T. L. J. Org. Chem. 1985, 50, 422. (c) For a review. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. (d) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 53-55. (e) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 108-111. (f) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 153-154. (g) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 339.
34. For selected references: (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843. (b) Mead, K.; MacDonald, T. L. J. Org. Chem. 1985, 50, 422. (c) For a review. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. (d) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 53-55. (e) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 108-111. (f) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 153-154. (g) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 339.
35. For selected references: (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843. (b) Mead, K.; MacDonald, T. L. J. Org. Chem. 1985, 50, 422. (c) For a review. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. (d) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 53-55. (e) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 108-111. (f) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 153-154. (g) Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 339.
36. (a) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
37. (b) Anh, N. T. Top. Curr. Chem. 1980, 88, 145.
38. (a) Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828.
39. (b) Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1963, 85, 1245.
40. Burke, S. D.; Hong, J.; Lennox, J. R.; Mongin, A. P. J. Org. Chem. 1998, 63, 6952.
41. (a) Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun. 1985, 1636.
42. (b) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728.
43. (c) Kusakabe, M.; Sato, F. J. Chem. Soc., Chem. Commun. 1986, 989.
44. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597.
45. Yamanoi, T.; Akiyama, T.; Ishida, E.; Abe, H.; Amemiya, M.; Inazu, T. Chem. Lett. 1989, 335.
46. (a) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979.
47. (b) Koskinen, P. M.; Koskinen, A. M. P. Methods Enzymol. 2000, 311, 458.
48. (c) Chun, J.; Li, G.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2002, 67, 2600.
49. Goundry, W. R. F. Synlett 2003, 1940; and references cited therein.
50. Wipf, P.; Stephenson, C. R. J. Org. Lett. 2003, 5, 2449.
51. Shinokubo, H.; Miki, H.; Yokoo, T.; Oshima, K.; Utimoto, K. Tetrahedron 1995, 51, 11681.