Enantioselective conjugate addition of diethylzinc to cyclohexenone catalyzed by a chiral aminophosphine-copper(II) triflate

Tetrahedron Asymmetry

Volumn 9, Issue 18, 1998, Pages 3175-3178

  Mori, Toshiyuki ^a   Kosaka, Kyoko ^a   Nakagawa, Yuichi ^a   Nagaoka, Yasuo ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; 4,4 DIMETHYLCYCLOHEXENONE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ALKYLATION; CATALYSIS; CHIRALITY; COLUMN CHROMATOGRAPHY; CONJUGATION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; LIGAND BINDING; PRIORITY JOURNAL; REVIEW;

EID: 0032544803     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00348-6     Document Type: Article

References (43)

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2. 1. Reviews of asymmetric reactions of organocopper: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806; Kanai, M.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 54, 474-480; Krause, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 283-285; Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds; Springer: New York, 1998.
3. 1. Reviews of asymmetric reactions of organocopper: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806; Kanai, M.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 54, 474-480; Krause, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 283-285; Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds; Springer: New York, 1998.
4. 1. Reviews of asymmetric reactions of organocopper: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806; Kanai, M.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 54, 474-480; Krause, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 283-285; Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds; Springer: New York, 1998.
5. 2. Recently reported chirally modified heterocuprate in catalytic conjugate addition reaction: Wendisch, V.; Sewald, N. Tetrahedron: Asymmetry 1997, 8, 1253-1257; de Vries, A. H. M.; Hof, R. P.; Staal, D.; Kellogg, R. M.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1539-1543.
6. 2. Recently reported chirally modified heterocuprate in catalytic conjugate addition reaction: Wendisch, V.; Sewald, N. Tetrahedron: Asymmetry 1997, 8, 1253-1257; de Vries, A. H. M.; Hof, R. P.; Staal, D.; Kellogg, R. M.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1539-1543.
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9. 3. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Kanai, M.; Koga, K.; Tomioka, K. J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4273-4274; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1996, 37, 7805-7808; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron 1998, 54, 10295-10307. Other ligands based on this line: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. Abstract 2 of the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, p. 79; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
10. 3. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Kanai, M.; Koga, K.; Tomioka, K. J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4273-4274; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1996, 37, 7805-7808; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron 1998, 54, 10295-10307. Other ligands based on this line: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. Abstract 2 of the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, p. 79; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
11. 3. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Kanai, M.; Koga, K.; Tomioka, K. J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4273-4274; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1996, 37, 7805-7808; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron 1998, 54, 10295-10307. Other ligands based on this line: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. Abstract 2 of the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, p. 79; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
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31. 10. Recently reported copper(II) triflate-chiral phosphine approaches: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; Alexakis, A.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 7745-7748; Alexakis, A.; Burton, J.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 3987-3990; Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Synlett 1997, 1429-1431; Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409-2413.
32. 10. Recently reported copper(II) triflate-chiral phosphine approaches: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; Alexakis, A.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 7745-7748; Alexakis, A.; Burton, J.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 3987-3990; Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Synlett 1997, 1429-1431; Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409-2413.
33. 10. Recently reported copper(II) triflate-chiral phosphine approaches: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; Alexakis, A.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 7745-7748; Alexakis, A.; Burton, J.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 3987-3990; Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Synlett 1997, 1429-1431; Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409-2413.
34. 10. Recently reported copper(II) triflate-chiral phosphine approaches: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; Alexakis, A.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 7745-7748; Alexakis, A.; Burton, J.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 3987-3990; Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Synlett 1997, 1429-1431; Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409-2413.
35. 10. Recently reported copper(II) triflate-chiral phosphine approaches: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623; Alexakis, A.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 7745-7748; Alexakis, A.; Burton, J.; Vastra, J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 3987-3990; Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Synlett 1997, 1429-1431; Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409-2413.
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42. 3) in 55% ee.
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