Rhodium-Catalyzed Asymmetric 1,6-Addition of Aryltitanates to Enynones Giving Axially Chiral Allenes

Organic Letters

Volumn 6, Issue 2, 2004, Pages 305-309

  Hayashi, Tamio ^a   Tokunaga, Norihito ^a   Inoue, Kazuya ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; CHLOROTRIMETHYLSILANE; ETHER DERIVATIVE; LITHIUM DERIVATIVE; REAGENT; RHODIUM COMPLEX; SILANE DERIVATIVE; TITANIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; METHODOLOGY;

EID: 0842285210     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036309f     Document Type: Article

References (41)

1. For reviews: (a) The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982. (b) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590. (d) Krause, N.; Hoffmann-Röder, A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, p 145.
2. For reviews: (a) The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982. (b) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590. (d) Krause, N.; Hoffmann-Röder, A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, p 145.
3. For reviews: (a) The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982. (b) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590. (d) Krause, N.; Hoffmann-Röder, A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, p 145.
4. For reviews: (a) The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982. (b) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590. (d) Krause, N.; Hoffmann-Röder, A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, p 145.
5. For a relevant review on the enantioselective synthesis of allenes: Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2002, 41, 2933.
6. Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468.
7. Han, J. W.; Tokunaga, N.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 12915.
8. (a) Tillack, A.; Michalik, D.; Koy, C.; Michalik, M. Tetrahedron Lett. 1999, 40, 6567.
9. (b) Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116.
10. (a) Ogasawara, M.; Ikeda, H.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 2089.
11. (b) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217.
12. (c) Imada, Y.; Ueno, K.; Kutsuwa, K.; Murahashi, S.-I. Chem. Lett. 2002, 140.
13. (a) Fredrick, M. A.; Hulce, M. Tetrahedron 1997, 53, 10197 and references therein.
14. (b) Cheng, M.; Hulce, M. J. Org. Chem. 1990, 55, 964.
15. (c) Hulce, M. Tetrahedron Lett. 1988, 29, 5851.
16. (a) For a relevant review: Krause, N.; Thorand, S. Inorg. Chim. Acta 1999, 296, 1.
17. (b) Canisius, J.; Gerold, A.; Krause, N. Angew. Chem., Int. Ed. 1999, 38, 1644 and references therein.
18. (c) Krause, N. Chem. Ber. 1990, 123, 2173.
19. Fu, X.; Zhang, S.; Yin, J.; Schumacher, D. P. Tetrahedron Lett. 2002, 43, 6673.
20. (a) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
21. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479.
22. (c) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
23. (d) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957.
24. (e) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591.
25. (f) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
26. (g) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852.
27. (h) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
28. (a) Hayashi, T.; Tokunaga, N.; Yoshida, K.; Han, J. W. J. Am. Chem. Soc. 2002, 124, 12102.
29. (b) Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 2872.
30. (a) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932.
31. (b) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083.
32. (c) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791.
33. (d) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681.
34. For reviews: (a) Hayashi, T. Synlett 2001, 879. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
35. For reviews: (a) Hayashi, T. Synlett 2001, 879. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
36. For reviews: (a) Hayashi, T. Synlett 2001, 879. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
37. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
38. 2O (10/1), 100°C, 3 h) (see ref 10) gave only a small amount (7%) of the dienyl ketone 7am.
39. 3 in the absence of the rhodium catalyst at 20°C for 0.5 h gave ca. 70% yield of the silyl ether 3am.
40. Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
41. 4Li (2m), gives silyl enol ether and phenyl-rhodium species (see also ref 11a).