Remarkable effect of tris(4-fluorophenyl)phosphine oxide on the stabilization of chiral lanthanum complex catalysts. A new and practical protocol for the highly enantioselective epoxidation of conjugated enones

Organic and Biomolecular Chemistry

Volumn 2, Issue 13, 2004, Pages 1822-1824

  Kino, Rie ^a   Daikai, Kazuhiro ^a   Kawanami, Toshio ^a   Fumno, Hiroshi ^a   Inanaga, Junji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; LANTHANUM COMPOUNDS; MIXTURES; OLIGOMERS; OXIDATION; X RAY CRYSTALLOGRAPHY;

ACHIRAL LIGANDS; CHIRAL CATALYST SYSTEMS; ENANTIOSELECTIVITY; LIGAND EXCHANGE;

ORGANIC COMPOUNDS;

EID: 3142739528     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b405882h     Document Type: Article

References (21)

1. For recent review, see: (a) C. Lauret and S. M. Roberts, Aldrichim. Acta, 2002, 35, 47; (b) M. J. Porter and J. Skidmore, Chem. Commun., 2000, 1215.
2. For recent review, see: (a) C. Lauret and S. M. Roberts, Aldrichim. Acta, 2002, 35, 47; (b) M. J. Porter and J. Skidmore, Chem. Commun., 2000, 1215.
3. (a) M. Bougauchi, S. Watanabe, T. Aral, H. Sasai and M. Shibasaki, J. Am. Chem. Soc., 1997, 119, 2329;
4. (b) S. Watanabe, Y. Kobayashi, T. Aral, H. Sasai, M. Bougauchi and M. Shibasaki, Tetrahedron Lett., 1998, 39, 7353;
5. (c) S. Watanabe, T. Aral, H. Sasai, M. Bougauchi and M. Shibasaki, J. Org. Chem., 1998, 63, 8090.
6. (a) K. Daikai, M. Kamaura and J. Inanaga, Tetrahedron Lett., 1998, 39, 7321;
7. (b) K. Daikai, T. Hayano, R. Kino, H. Furuno, T. Kagawa and I Inanaga, Chirality, 2003, 15, 83;
8. (c) J. Inanaga, H. Furuno and T. Hayano, Chem. Rev., 2002, 102, 2211.
9. A similar catalyst system using triphenylarsine oxide in place of triphenylphosphine oxide has been extensively and successfully studied: (a) T. Nemoto, T. Ohshima and M. Shibasaki, Tetrahedron Lett., 2000, 41, 9569; (b) T. Nemoto, T. Ohshima, K. Yamaguchi and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 2725; T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2003, 42, 4680; T. Ohshima, T. Nemoto, S. Tosaki, H. Kakei, V. Gnanadesikan and M. Shibasaki, Tetrahedron, 2003, 59, 10485 and references cited therein.
10. A similar catalyst system using triphenylarsine oxide in place of triphenylphosphine oxide has been extensively and successfully studied: (a) T. Nemoto, T. Ohshima and M. Shibasaki, Tetrahedron Lett., 2000, 41, 9569; (b) T. Nemoto, T. Ohshima, K. Yamaguchi and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 2725; T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2003, 42, 4680; T. Ohshima, T. Nemoto, S. Tosaki, H. Kakei, V. Gnanadesikan and M. Shibasaki, Tetrahedron, 2003, 59, 10485 and references cited therein.
11. A similar catalyst system using triphenylarsine oxide in place of triphenylphosphine oxide has been extensively and successfully studied: (a) T. Nemoto, T. Ohshima and M. Shibasaki, Tetrahedron Lett., 2000, 41, 9569; (b) T. Nemoto, T. Ohshima, K. Yamaguchi and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 2725; T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2003, 42, 4680; T. Ohshima, T. Nemoto, S. Tosaki, H. Kakei, V. Gnanadesikan and M. Shibasaki, Tetrahedron, 2003, 59, 10485 and references cited therein.
12. A similar catalyst system using triphenylarsine oxide in place of triphenylphosphine oxide has been extensively and successfully studied: (a) T. Nemoto, T. Ohshima and M. Shibasaki, Tetrahedron Lett., 2000, 41, 9569; (b) T. Nemoto, T. Ohshima, K. Yamaguchi and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 2725; T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2003, 42, 4680; T. Ohshima, T. Nemoto, S. Tosaki, H. Kakei, V. Gnanadesikan and M. Shibasaki, Tetrahedron, 2003, 59, 10485 and references cited therein.
13. For other lanthanide-catalyzed epoxidations of conjugated enones, see: (a) R. Chen, C. Qian and J. G. de Vries, Tetrahedron, 2001, 57, 9837; (b) D. Jayaprakash, Y. Kobayashi, T. Arai, Q.-S. Hu, X.-F. Zheng, L. Pu and H. Sasai, J. Mol. Catal. A, 2003, 196, 145.
14. For other lanthanide-catalyzed epoxidations of conjugated enones, see: (a) R. Chen, C. Qian and J. G. de Vries, Tetrahedron, 2001, 57, 9837; (b) D. Jayaprakash, Y. Kobayashi, T. Arai, Q.-S. Hu, X.-F. Zheng, L. Pu and H. Sasai, J. Mol. Catal. A, 2003, 196, 145.
15. The protocol was successfully applied to large-scale experiments (e.g., 80 kg scale; 90% chemical yield, 98% ee): private communication from Mr T. Kagawa (Tosoh Corporation, Japan).
16. 3PO = 1: 1: 1] gave a slightly worse result (93% ee, 91% yield; unpublished).
17. (a) W. Krouti, M. E. Lasterra-Sánchez, S. J. Maddrall, P. Mayon, P. Morgan, S. M. Roberts, S. R. Thornton, C. J. Todd and M. Tüter, J. Chem. Soc., Perkins Trans. 1, 1996, 2837;
18. (b) B. Lygo and P. G. Wainwright, Tetrahedron, 1999, 55, 6289;
19. (c) W. Adam, P. B. Rao, H.-G. Degen and C. R. Saha-Möller, J. Am. Chem. Soc., 2000, 122, 5654.
20. 2) = 0.2872. CCDC reference number 224162. See http://www.rsc.org/suppdata/ob/b4/b405882h/ for crystallographic data in.cif or other electronic format.
21. Purchased from Fuji Silysia Chemical Ltd., Japan