Catalytic asymmetric arylative cyclization of alkynals: Phosphine-free rhodium/diene complexes as efficient catalysts

Journal of the American Chemical Society

Volumn 127, Issue 1, 2005, Pages 54-55

  Shintani, Ryo ^a   Okamoto, Kazuhiro ^a   Otomaru, Yusuke ^a   Ueyama, Kazuhito ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYL GROUP; ALKYNAL; ALLYL COMPOUND; FUNCTIONAL GROUP; LIGAND; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; CATALYST; COMPLEX FORMATION; CYCLIZATION; LIGAND BINDING; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 11844251240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044021v     Document Type: Article

References (34)

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16. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
17. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
18. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
19. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
20. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
21. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
22. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
23. Similar reactions have been reported by the use of other transition metals. (a) Nickel catalysis with organozinc reagents: Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. See also: Montgomery, J. Acc. Chem. Res. 2000, 33, 467. (b) Nickel catalysis with organozirconium reagents: Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. (c) Nickel catalysis with organoboron reagents (for allylamine synthesis): Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941. Iron catalysis with organolithium reagents: (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621. Manganese catalysis with Grignard reagents: (e) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061. Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 11.
24. Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
25. These reactions with bisphosphine ligands typically result in the recovery of unreacted alkynal 1a as the major component.
26. To date, we have not been able to achieve intermolecular three-component couplings of organoboronic acids, alkynes, and aldehydes.
27. (a) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.
28. (b) Shintani, R.; Ueyama, K.; Yamada, I.; Hayashi, T. Org. Lett. 2004, 6, 3425.
29. For an overview, see: (c) Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364.
30. (a) Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584.
31. See also: (b) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628. (c) Defieber, C.; Paquin, J.-F.; Serna, S.; Carreira, E. M. Org. Lett. 2004, 6, 3873.
32. See also: (b) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628. (c) Defieber, C.; Paquin, J.-F.; Serna, S.; Carreira, E. M. Org. Lett. 2004, 6, 3873.
33. Alkylboronic acids are not suitable nucleophiles under the same reaction conditions.
34. See refs 3c and 3d for intramolecular insertion of alkyl-rhodium species to electron-deficient olefins.