Structural requirements of an external, chiral amidophosphine ligand for asymmetric reaction of an organocopper reagent

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7805-7808

  Nakagawa, Yuichi ^b   Kanai, Motomu ^a   Nagaoka, Yasuo ^b   Tomioka, Kiyoshi ^b  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; KETONE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 16044372279     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01783-2     Document Type: Article

References (47)

1. 1. Tomioka, K. Synthesis 1990, 541-549; Noyori, R. Asymmetric Catalysis in Organic Synthesis John Wiley and Sons, Inc. New York, 1994; Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999-1004.
2. 1. Tomioka, K. Synthesis 1990, 541-549; Noyori, R. Asymmetric Catalysis in Organic Synthesis John Wiley and Sons, Inc. New York, 1994; Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999-1004.
3. 1. Tomioka, K. Synthesis 1990, 541-549; Noyori, R. Asymmetric Catalysis in Organic Synthesis John Wiley and Sons, Inc. New York, 1994; Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999-1004.
4. 2. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Idem, J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Idem, ibid. 1995, 36, 4273-4274; Idem, ibid. 1995, 36, 4275-4278.
5. 2. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Idem, J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Idem, ibid. 1995, 36, 4273-4274; Idem, ibid. 1995, 36, 4275-4278.
6. 2. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Idem, J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Idem, ibid. 1995, 36, 4273-4274; Idem, ibid. 1995, 36, 4275-4278.
7. 2. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Idem, J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Idem, ibid. 1995, 36, 4273-4274; Idem, ibid. 1995, 36, 4275-4278.
8. 2. Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett. 1992, 33, 7193-7196; Idem, J. Chem. Soc., Chem. Commun. 1993, 1248-1249; Kanai, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 895-898; Idem, ibid. 1995, 36, 4273-4274; Idem, ibid. 1995, 36, 4275-4278.
9. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
10. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
11. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
12. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
13. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
14. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
15. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
16. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
17. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
18. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
19. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
20. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
21. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
22. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
23. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
24. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
25. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
26. 3. Chirally modified heterocuprate in stoichiometric conjugate addition reaction: Zweig, J. S.; Luche, J. L.; Barreiro, E.; Crabbé, P. Tetrahedron Lett. 1975, 2355-2358; Mukaiyama, T.; Imamoto, T. Chem. Lett. 1980, 45-46; Huché, M.; Berlan, J.; Pourcelot, G.; Cresson, P. Tetrahedron Lett. 1981, 22, 1329-1332; Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953-4959; Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116; Tanaka, K.; Ushio, H; Suzuki, H. J. Chem. Soc., Chem. Commun. 1990, 795-797; Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W. Tetrahedron Lett. 1990, 31, 4105-4108; Quinkert, G.; Müller, T.; Königer, A.; Schrtheis, O.; Sickenberger, B.; Düner, G. Tetrahedron Lett. 1992, 33, 3469-3472; Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986; Swingle, N. M.; Reddy, K. V.; Rossiter, B. E. Tetrahedron 1994, 50, 4455-4466. Chirally modified heterocuprate in catalytic conjugate addition reaction: Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175-3182; Ahn, K.-H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178-3181; Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry 1991, 2, 1097-1100; Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 3400-3410; Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219-1230; Zhou, Q.-L.; Pfaltz, A Tetrahedron Lett. 1993, 34, 7725-7728; Idem, Tetrahedron 1994, 50, 4467-4478; van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135-6138.
27. 4. Review for asymmetric reaction 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.
28. 4. Review for asymmetric reaction 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.
29. 5. Alexakis, A.; Mutti, S.; Normant, J. F. J. Am. Chem. Soc. 1991, 113, 6332-6334; Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427-2430.
30. 5. Alexakis, A.; Mutti, S.; Normant, J. F. J. Am. Chem. Soc. 1991, 113, 6332-6334; Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427-2430.
31. 6. External, chiral diamine ligand: Kretchmer, R. A. J. Org. Chem. 1972, 37, 2744-2747.
32. 7. Leyendecker, F.; Laucher, D. Tetrahedron Lett. 1983, 24, 3517-3520; Idem, Nouv. J. Chim. 1985, 9, 13-19.
33. 7. Leyendecker, F.; Laucher, D. Tetrahedron Lett. 1983, 24, 3517-3520; Idem, Nouv. J. Chim. 1985, 9, 13-19.
34. 3).
35. 9. Ogata, I.; Mizukami, F.; Ikeda, Y.; Tanaka, M. Japan Patent, Kokai, 1976, 76, 43754; Chem. Abstr. 1976, 85: 124144z.
36. 9. Ogata, I.; Mizukami, F.; Ikeda, Y.; Tanaka, M. Japan Patent, Kokai, 1976, 76, 43754; Chem. Abstr. 1976, 85: 124144z.
37. 10. Davies, S, G.; Doisneau, G. J.-M.; Prodger, J. C.; Sanganee, H. J. Tetrahedron Lett. 1994, 35, 2369-2372.
38. 11. Ee was determined by HPLC analysis (Daicel Chiral Pak AD, i-PrOH/hexane 1/30, 0.5 mL/min, (S) 14 min, (R) 17 min). The absolute configuration was determined by specific rotation. Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4011-4018.
39. 12. This was unambiguously confirmed by X-ray crystallography of 1. Detail will be described elsewhere.
40. 13. Pearson, R. G.; Gregory, C. D. J. Am. Chem. Soc. 1976, 98, 4098-4104: Ashby, E. C.; Watkins, J. J. ibid. 1977, 99, 5312-5317; Lipshutz, B. H.; Kozlowski, J. A.; Breneman, C. M. ibid. 1985, 107, 3197-3204; Stewart, K. R.; Lever, J. R.; Whangbo, M.-H. J. Org. Chem. 1982, 47, 1472-1474; Lorenzen, N. P.; Weiss, E. Angew. Chem. Int. Ed. Engl. 1990, 29, 300-302; Olmstead, M. M.; Power, P. P. Organometallics, 1990, 9, 1720-1722.
41. 13. Pearson, R. G.; Gregory, C. D. J. Am. Chem. Soc. 1976, 98, 4098-4104: Ashby, E. C.; Watkins, J. J. ibid. 1977, 99, 5312-5317; Lipshutz, B. H.; Kozlowski, J. A.; Breneman, C. M. ibid. 1985, 107, 3197-3204; Stewart, K. R.; Lever, J. R.; Whangbo, M.-H. J. Org. Chem. 1982, 47, 1472-1474; Lorenzen, N. P.; Weiss, E. Angew. Chem. Int. Ed. Engl. 1990, 29, 300-302; Olmstead, M. M.; Power, P. P. Organometallics, 1990, 9, 1720-1722.
42. 13. Pearson, R. G.; Gregory, C. D. J. Am. Chem. Soc. 1976, 98, 4098-4104: Ashby, E. C.; Watkins, J. J. ibid. 1977, 99, 5312-5317; Lipshutz, B. H.; Kozlowski, J. A.; Breneman, C. M. ibid. 1985, 107, 3197-3204; Stewart, K. R.; Lever, J. R.; Whangbo, M.-H. J. Org. Chem. 1982, 47, 1472-1474; Lorenzen, N. P.; Weiss, E. Angew. Chem. Int. Ed. Engl. 1990, 29, 300-302; Olmstead, M. M.; Power, P. P. Organometallics, 1990, 9, 1720-1722.
43. 13. Pearson, R. G.; Gregory, C. D. J. Am. Chem. Soc. 1976, 98, 4098-4104: Ashby, E. C.; Watkins, J. J. ibid. 1977, 99, 5312-5317; Lipshutz, B. H.; Kozlowski, J. A.; Breneman, C. M. ibid. 1985, 107, 3197-3204; Stewart, K. R.; Lever, J. R.; Whangbo, M.-H. J. Org. Chem. 1982, 47, 1472-1474; Lorenzen, N. P.; Weiss, E. Angew. Chem. Int. Ed. Engl. 1990, 29, 300-302; Olmstead, M. M.; Power, P. P. Organometallics, 1990, 9, 1720-1722.
44. 13. Pearson, R. G.; Gregory, C. D. J. Am. Chem. Soc. 1976, 98, 4098-4104: Ashby, E. C.; Watkins, J. J. ibid. 1977, 99, 5312-5317; Lipshutz, B. H.; Kozlowski, J. A.; Breneman, C. M. ibid. 1985, 107, 3197-3204; Stewart, K. R.; Lever, J. R.; Whangbo, M.-H. J. Org. Chem. 1982, 47, 1472-1474; Lorenzen, N. P.; Weiss, E. Angew. Chem. Int. Ed. Engl. 1990, 29, 300-302; Olmstead, M. M.; Power, P. P. Organometallics, 1990, 9, 1720-1722.
45. 13. Pearson, R. G.; Gregory, C. D. J. Am. Chem. Soc. 1976, 98, 4098-4104: Ashby, E. C.; Watkins, J. J. ibid. 1977, 99, 5312-5317; Lipshutz, B. H.; Kozlowski, J. A.; Breneman, C. M. ibid. 1985, 107, 3197-3204; Stewart, K. R.; Lever, J. R.; Whangbo, M.-H. J. Org. Chem. 1982, 47, 1472-1474; Lorenzen, N. P.; Weiss, E. Angew. Chem. Int. Ed. Engl. 1990, 29, 300-302; Olmstead, M. M.; Power, P. P. Organometallics, 1990, 9, 1720-1722.
46. 13C-NMR analysis of the corresponding diastereomeric ketals prepared with (R,R)-2,3-butanediol. The absolute configuration was determined by specific rotation. See reference 3 by Corey et al.
47. 3)) in 92% ee and 82% yield.