An external chiral amidophosphine ligand for asymmetric conjugate addition of organocopper

Tetrahedron

Volumn 54, Issue 35, 1998, Pages 10295-10307

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

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; LIGAND; PHOSPHINE DERIVATIVE;

ARTICLE; CHIRALITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032572892     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00485-2     Document Type: Article

References (52)

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. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron 1997, 53, 10699-10708; Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm.Bull. 1997, 4, 1705-1707; Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973-8976.
5. 2. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron 1997, 53, 10699-10708; Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm.Bull. 1997, 4, 1705-1707; Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973-8976.
6. 2. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron 1997, 53, 10699-10708; Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm.Bull. 1997, 4, 1705-1707; Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973-8976.
7. 2. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron 1997, 53, 10699-10708; Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm.Bull. 1997, 4, 1705-1707; Asano, Y.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973-8976.
8. 3. Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061.
9. 4. Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. in press.
10. 5. Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. in press.
11. 6. 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; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. ibid. 1996, 37, 7805-7808. Other ligands: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract Paper 2, p. 79.
12. 6. 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; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. ibid. 1996, 37, 7805-7808. Other ligands: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract Paper 2, p. 79.
13. 6. 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; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. ibid. 1996, 37, 7805-7808. Other ligands: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract Paper 2, p. 79.
14. 6. 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; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. ibid. 1996, 37, 7805-7808. Other ligands: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract Paper 2, p. 79.
15. 6. 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; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. ibid. 1996, 37, 7805-7808. Other ligands: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract Paper 2, p. 79.
16. 6. 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; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. ibid. 1996, 37, 7805-7808. Other ligands: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract Paper 2, p. 79.
17. 6. 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; Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. ibid. 1996, 37, 7805-7808. Other ligands: Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. presented at the 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract Paper 2, p. 79.
18. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
19. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
20. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
21. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
22. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
23. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
24. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
25. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
26. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
27. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
28. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
29. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
30. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
31. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
32. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
33. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
34. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
35. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
36. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
37. 7. 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 Klareren, 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; 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. ibid. 1997, 8, 1539-1543.
38. 8. 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.
39. 8. 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.
40. 9. 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; de Vries, A. H.; Meestsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374-2376; Alexakis, A.; Vastra, J.; Burton, J.; Mangeney, P. Tetrahedron Asymmetry 1997, 8, 3193-3196; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
41. 9. 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; de Vries, A. H.; Meestsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374-2376; Alexakis, A.; Vastra, J.; Burton, J.; Mangeney, P. Tetrahedron Asymmetry 1997, 8, 3193-3196; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
42. 9. 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; de Vries, A. H.; Meestsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374-2376; Alexakis, A.; Vastra, J.; Burton, J.; Mangeney, P. Tetrahedron Asymmetry 1997, 8, 3193-3196; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
43. 9. 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; de Vries, A. H.; Meestsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374-2376; Alexakis, A.; Vastra, J.; Burton, J.; Mangeney, P. Tetrahedron Asymmetry 1997, 8, 3193-3196; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
44. 9. 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; de Vries, A. H.; Meestsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374-2376; Alexakis, A.; Vastra, J.; Burton, J.; Mangeney, P. Tetrahedron Asymmetry 1997, 8, 3193-3196; Stangeland, E. L.; Sammakia, T. Tetrahedron 1997, 53, 16503-16510.
45. 10. External, chiral diamine ligand: Kretchmer, R. A. J. Org. Chem. 1972, 37, 2744-2747.
46. 11. Leyendecker, F.; Laucher, D. Tetrahedron Lett. 1983, 24, 3517-3520; Idem, Nouv. J. Chim. 1985, 9, 13-19.
47. 11. Leyendecker, F.; Laucher, D. Tetrahedron Lett. 1983, 24, 3517-3520; Idem, Nouv. J. Chim. 1985, 9, 13-19.
48. 12. Davies, S. G.; Doisneau, G. J.-M.; Prodger, J. C.; Sanganee, H. J. Tetrahedron Lett. 1994, 35, 2369-2372.
49. 13. Ee was determined by HPLC analysis (Daicel ChiralPak AD, i-PrOH/hexane 1/30, 0.5 mL/min, (S) 14 min, (R) 17 min). The absolute configuration was determined by specific rotation. R=Me: Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4011-4018 ; R=Bu: Ahllerecht, H.; Sommer, H. Chem. Ber. 1990, 123, 829.
50. 13. Ee was determined by HPLC analysis (Daicel ChiralPak AD, i-PrOH/hexane 1/30, 0.5 mL/min, (S) 14 min, (R) 17 min). The absolute configuration was determined by specific rotation. R=Me: Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4011-4018 ; R=Bu: Ahllerecht, H.; Sommer, H. Chem. Ber. 1990, 123, 829.
51. 14. Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114-7116.
52. 15. Melting points were measured using a Yamato MODEL MP-21 melting point apparatus and are not corrected. Optical rotations were taken with a Jasco DIP-370 polarimeter. IR spectra were taken with a HITACHI infrared spectrometer model 260-10. 1H-NMR spectra were taken with a JEOL GX-270 spectrometer at 270 MHz, a HITACHI R-90H spectrometer at 90 MHz, in CDCl3 unless otherwise noted. 13C-NMR spectra were taken with a JEOL GX-270 spectrometer at 67 Mhz in CDCl3 unless otherwise noted Chemical shift values are expressed in ppm relative to internal tetramethylsilane. Abbreviations are as follows: s, singlet; d, doublet; t, triplet; m, multiplet. MS were taken with a JEOL-01, SG-2 mass spectrometer or a JEOL DX-300 mass spectrometer.