Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters

Tetrahedron Asymmetry

Volumn 10, Issue 20, 1999, Pages 4047-4056

  Takaya, Yoshiaki ^a   Senda, Taichi ^a   Kurushima, Hiroaki ^a   Ogasawara, Masamichi ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; ESTER DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033430294     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00417-6     Document Type: Article

References (28)

1. For reviews, see: (a) Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
2. For reviews, see: (a) Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
3. Examples of stoichiometric asymmetric 1,4-addition to α,β-unsaturated esters: (a) Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 115, 10139. (b) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109. (c) Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K. J. Am. Chem. Soc. 1995, 117, 12159. (d) Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973. (e) Frey, L. F.; Tillyer, R. D.; Caille, A. S.; Tschaen, D. M.; Dolling, U. H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 3120. (f) Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651.
4. Examples of stoichiometric asymmetric 1,4-addition to α,β-unsaturated esters: (a) Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 115, 10139. (b) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109. (c) Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K. J. Am. Chem. Soc. 1995, 117, 12159. (d) Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973. (e) Frey, L. F.; Tillyer, R. D.; Caille, A. S.; Tschaen, D. M.; Dolling, U. H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 3120. (f) Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651.
5. Examples of stoichiometric asymmetric 1,4-addition to α,β-unsaturated esters: (a) Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 115, 10139. (b) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109. (c) Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K. J. Am. Chem. Soc. 1995, 117, 12159. (d) Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973. (e) Frey, L. F.; Tillyer, R. D.; Caille, A. S.; Tschaen, D. M.; Dolling, U. H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 3120. (f) Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651.
6. Examples of stoichiometric asymmetric 1,4-addition to α,β-unsaturated esters: (a) Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 115, 10139. (b) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109. (c) Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K. J. Am. Chem. Soc. 1995, 117, 12159. (d) Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973. (e) Frey, L. F.; Tillyer, R. D.; Caille, A. S.; Tschaen, D. M.; Dolling, U. H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 3120. (f) Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651.
7. Examples of stoichiometric asymmetric 1,4-addition to α,β-unsaturated esters: (a) Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 115, 10139. (b) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109. (c) Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K. J. Am. Chem. Soc. 1995, 117, 12159. (d) Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973. (e) Frey, L. F.; Tillyer, R. D.; Caille, A. S.; Tschaen, D. M.; Dolling, U. H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 3120. (f) Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651.
8. Examples of stoichiometric asymmetric 1,4-addition to α,β-unsaturated esters: (a) Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 115, 10139. (b) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109. (c) Tanaka, F.; Node, M.; Tanaka, K.; Mizuchi, M.; Hosoi, S.; Nakayama, M.; Taga, T.; Fuji, K. J. Am. Chem. Soc. 1995, 117, 12159. (d) Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973. (e) Frey, L. F.; Tillyer, R. D.; Caille, A. S.; Tschaen, D. M.; Dolling, U. H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 3120. (f) Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651.
9. (a) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681.
10. (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431.
11. (c) Tomioka, K.; Kanai, M. Tetrahedron Lett. 1995, 36, 4275.
12. (d) Asano, Y.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1998, 46, 184.
13. (e) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803.
14. (f) Kanai, M.; Nakagawa, Y.; Tomioka, K. Tetrahedron 1999, 55, 3843.
15. Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229.
16. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
17. Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479.
18. Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957.
19. (a) Mukaiyama, T.; Iwasawa, N. Chem. Lett. 1981, 913.
20. (b) Touet, J.; Baudouin, S.; Brown, E. Tetrahedron: Asymmetry 1992, 3, 587.
21. (a) Irwin, A. J.; Jones, J. B. J. Am. Chem. Soc. 1977, 99, 556.
22. (b) Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. 1 1983, 2629.
23. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T. Organometallics 1993, 12, 4188.
24. Cramer, R. Inorg. Synth. 1974, 15, 16.
25. (a) Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1989, 67, 20.
26. (b) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
27. (a) Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316.
28. (b) Hawthorene, M. F. J. Am. Chem. Soc. 1958, 80, 4291.