Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5500-5511

  Li, Xiaolin ^a   Hewgley, J Brian ^a   Mulrooney, Carol A ^a   Yang, Jaemoon ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

CATALYSIS; CATALYSTS; CHELATION; COMPLEXATION; COPPER; DERIVATIVES; ESTERS; OXIDATION; OXYGEN; SUBSTRATES;

REACTION KINETICS;

1,5 DIAZADECALIN; 2 NAPHTHOL DERIVATIVE; COPPER COMPLEX; COPPER ION; DECALIN DERIVATIVE; ESTER DERIVATIVE; HYDROXYL GROUP; KETONE DERIVATIVE; LIGAND; NAPHTHALENE; NAPHTHOL DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHELATION; CHIRALITY; ENANTIOSELECTIVITY; OXIDATION; OXIDATION REDUCTION POTENTIAL; PRODUCTIVITY;

EID: 0038676302     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0340206     Document Type: Article

References (140)

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24. For some recent disclosures on the utility of substituted BINOL derivatives (see also refs 42-48 and 50-53), see: (a) Tsang, W. C. P.; Schrock, R. R.; Hoveyda, A. H. Organometallics 2001, 20, 5658-5669. (b) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett, 2001, 3, 4083-4085. (c) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735-1738. (d) Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952-4953. (e) Zhou, Y.-G.; Zhang, X. J. Chem. Soc., Chem. Commun. 2002, 1124-1125.
25. For some recent disclosures on the utility of substituted BINOL derivatives (see also refs 42-48 and 50-53), see: (a) Tsang, W. C. P.; Schrock, R. R.; Hoveyda, A. H. Organometallics 2001, 20, 5658-5669. (b) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett, 2001, 3, 4083-4085. (c) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735-1738. (d) Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952-4953. (e) Zhou, Y.-G.; Zhang, X. J. Chem. Soc., Chem. Commun. 2002, 1124-1125.
26. For some recent disclosures on the utility of substituted BINOL derivatives (see also refs 42-48 and 50-53), see: (a) Tsang, W. C. P.; Schrock, R. R.; Hoveyda, A. H. Organometallics 2001, 20, 5658-5669. (b) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett, 2001, 3, 4083-4085. (c) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735-1738. (d) Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952-4953. (e) Zhou, Y.-G.; Zhang, X. J. Chem. Soc., Chem. Commun. 2002, 1124-1125.
27. For some recent disclosures on the utility of substituted BINOL derivatives (see also refs 42-48 and 50-53), see: (a) Tsang, W. C. P.; Schrock, R. R.; Hoveyda, A. H. Organometallics 2001, 20, 5658-5669. (b) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett, 2001, 3, 4083-4085. (c) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735-1738. (d) Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952-4953. (e) Zhou, Y.-G.; Zhang, X. J. Chem. Soc., Chem. Commun. 2002, 1124-1125.
28. One of the most efficient routes to enantiomerically pure BINOL relies on a classical resolution employing a cinchonidine salt: (a) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126. For other resolution methods, see: (b) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302-4306. (c) Toda, F.; Tanaka, K. Chem. Commun. 1997, 1087-1088. (d) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126.(e) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 7991-7994. (f) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299-2300.
29. (a) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126. For other resolution methods, see: (b) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302-4306. (c) Toda, F.; Tanaka, K. Chem. Commun. 1997, 1087-1088. (d) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126.(e) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 7991-7994. (f) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299-2300.
30. (a) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126. For other resolution methods, see: (b) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302-4306. (c) Toda, F.; Tanaka, K. Chem. Commun. 1997, 1087-1088. (d) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126.(e) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 7991-7994. (f) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299-2300.
31. (a) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126. For other resolution methods, see: (b) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302-4306. (c) Toda, F.; Tanaka, K. Chem. Commun. 1997, 1087-1088. (d) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126.(e) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 7991-7994. (f) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299-2300.
32. (a) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126. For other resolution methods, see: (b) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302-4306. (c) Toda, F.; Tanaka, K. Chem. Commun. 1997, 1087-1088. (d) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126.(e) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 7991-7994. (f) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299-2300.
33. (a) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126. For other resolution methods, see: (b) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302-4306. (c) Toda, F.; Tanaka, K. Chem. Commun. 1997, 1087-1088. (d) Hu, Q.-S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123-2126.(e) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 7991-7994. (f) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299-2300.
34. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
35. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
36. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
37. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
38. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
39. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
40. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
41. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
42. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
43. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
44. The development of an efficient catalytic asymmetric BINOL synthesis has been the focus of several research groups: (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. Chem. Commun. 1993, 909-911. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4537. (c) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519-9520. (d) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271 (10 mol % catalyst, 78% ee for 9a, 17% ee for BINOL). (e) Irie, R.; Masutani, K.; Katsuki, I. Synlett 2000, 1453-1436 (2 mol % catalyst, 65% ee for BINOL). (f) Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980-981 (2 mol % catalyst, 51% ee for BINOL). (g) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869-872 (10 mol % catalyst, 62% ee for BINOL). (h) Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Chem. Commun. 2002, 914-915 (10 mol % catalyst, 6 d, 83% ee for BINOL). (i) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529-2532 (10 mol % catalyst, 15 d, 87% ee for BINOL). (j) Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532-4535 (10 mol % catalyst, 8 d, 90% ee for BINOL). (k) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53-55 (10 mol % catalyst, 73% ee for BINOL).
45. (a) Brussee, J.; Jansen, A. C. A. Tetrahedron Lett. 1983, 24, 3261-3262.
46. (b) Brussee, J.; Groenendijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313-3319.
47. (a) Yamamoto, K.; Fukushima, H.; Nakazaki, M. Chem. Commun. 1984, 1490-1491.
48. (b) Yamamoto, K.; Fukushima, H.; Yumioka, H.; Nakazaki, M. Bull. Chem. Soc. Jpn. 1985, 58, 3633-3634.
49. (a)Smrčina, M.; Lorenc, M.; Hanuš, V.; Sedmera, P.; Kočovský, P. J. Org. Chem. 1992, 57, 1917-1920.
50. (b) See also ref 9b, which describes one reaction with a copper catalyst using AgCl as the terminal oxidant.
51. (a) For our preliminary work in this area, see: Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137-1140.
52. (b) For application to 1,1′-binaphthyl polymerization, see: Xie, X.; Phuan, P.-W.; Kozlowski, M. C. Angew. Chem., Int. Ed. 2003, 42, 2168-2170.
53. (c) For application to perylenequinone precursors, see: Mulrooney, C. A.; Li, X.; DiVirgilio, E. S.; Kozlowski, M. C. J. Am. Chem. Soc. 2003, 125, 6856-6857.
54. For reviews of 1,2-diamines, see: (a) Lucet, D.; LeGall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627. (b) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3195. (c) Mukaiyama, T.; Asami, M. Top. Curr. Chem. 1985, 127, 133-167
55. For reviews of 1,2-diamines, see: (a) Lucet, D.; LeGall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627. (b) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3195. (c) Mukaiyama, T.; Asami, M. Top. Curr. Chem. 1985, 127, 133-167
56. For reviews of 1,2-diamines, see: (a) Lucet, D.; LeGall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627. (b) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3195. (c) Mukaiyama, T.; Asami, M. Top. Curr. Chem. 1985, 127, 133-167
57. For reviews of sparteine, see: (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316. (b) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
58. For reviews of sparteine, see: (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316. (b) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
59. Kozlowski, M. C.; Waters, S. P.; Skudlarek, J. W.; Evans, C. A. Org. Lett. 2002, 4, 4391-4393.
60. Ganguly, B.; Freed, D. A.; Kozlowski, M. C. J. Org. Chem. 2001, 66, 1103-1108.
61. (a) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875-878.
62. (b) Xu, Z.; Kozlowski, M. C. J. Org. Chem. 2002, 67, 3072-3078.
63. For Mn-promoted biaryl couplings, see: (a) Dewar, M. J. S.; Nakaya, T. J. Am. Chem. Soc. 1968, 90, 7134-7135. (b) Yamamoto, K.; Fukushima, H.; Okamoto, Y.; Hatada, K.; Nakazaki, M. Chem. Commun. 1984, 1111-1112.
64. For Mn-promoted biaryl couplings, see: (a) Dewar, M. J. S.; Nakaya, T. J. Am. Chem. Soc. 1968, 90, 7134-7135. (b) Yamamoto, K.; Fukushima, H.; Okamoto, Y.; Hatada, K.; Nakazaki, M. Chem. Commun. 1984, 1111-1112.
65. For Fe-promoted biaryl couplings, see: (a) Pummerer, R.; Prell, E.; Rieche, A. Chem. Ber. 1926, 59, 2159-2161. (b) Feringa, B.; Wynberg, H. J. Org. Chem. 1981, 46, 2547-2557. (c) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007-3009. (d) Ding, K.; Wang, Y.; Zhang, L.; Wu, Y.; Matsuura, T. Tetrahedron 1996, 52, 1005-1010. (e) Deussen, H.-J.; Frederiksen, P.; Bjoernholm, T.; Bechgaard, K. Org. Prep. Proc. Int. 1996, 28, 484-486.
66. For Fe-promoted biaryl couplings, see: (a) Pummerer, R.; Prell, E.; Rieche, A. Chem. Ber. 1926, 59, 2159-2161. (b) Feringa, B.; Wynberg, H. J. Org. Chem. 1981, 46, 2547-2557. (c) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007-3009. (d) Ding, K.; Wang, Y.; Zhang, L.; Wu, Y.; Matsuura, T. Tetrahedron 1996, 52, 1005-1010. (e) Deussen, H.-J.; Frederiksen, P.; Bjoernholm, T.; Bechgaard, K. Org. Prep. Proc. Int. 1996, 28, 484-486.
67. For Fe-promoted biaryl couplings, see: (a) Pummerer, R.; Prell, E.; Rieche, A. Chem. Ber. 1926, 59, 2159-2161. (b) Feringa, B.; Wynberg, H. J. Org. Chem. 1981, 46, 2547-2557. (c) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007-3009. (d) Ding, K.; Wang, Y.; Zhang, L.; Wu, Y.; Matsuura, T. Tetrahedron 1996, 52, 1005-1010. (e) Deussen, H.-J.; Frederiksen, P.; Bjoernholm, T.; Bechgaard, K. Org. Prep. Proc. Int. 1996, 28, 484-486.
68. For Fe-promoted biaryl couplings, see: (a) Pummerer, R.; Prell, E.; Rieche, A. Chem. Ber. 1926, 59, 2159-2161. (b) Feringa, B.; Wynberg, H. J. Org. Chem. 1981, 46, 2547-2557. (c) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007-3009. (d) Ding, K.; Wang, Y.; Zhang, L.; Wu, Y.; Matsuura, T. Tetrahedron 1996, 52, 1005-1010. (e) Deussen, H.-J.; Frederiksen, P.; Bjoernholm, T.; Bechgaard, K. Org. Prep. Proc. Int. 1996, 28, 484-486.
69. For Fe-promoted biaryl couplings, see: (a) Pummerer, R.; Prell, E.; Rieche, A. Chem. Ber. 1926, 59, 2159-2161. (b) Feringa, B.; Wynberg, H. J. Org. Chem. 1981, 46, 2547-2557. (c) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007-3009. (d) Ding, K.; Wang, Y.; Zhang, L.; Wu, Y.; Matsuura, T. Tetrahedron 1996, 52, 1005-1010. (e) Deussen, H.-J.; Frederiksen, P.; Bjoernholm, T.; Bechgaard, K. Org. Prep. Proc. Int. 1996, 28, 484-486.
70. Kozlowski, M. C.; Li, X.; Carroll, P. J.; Xu, Z. Organometallics 2002, 21, 4513-4522.
71. Other solvents were examined but provide no improvement: benzene, <5% yield, 67% ee; MeOH, 68% yield, 65% ee.
72. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988; p 758.
73. (a) Frenna, V.; Vivona, N.; Consiglio, G.; Spinelli, D. J. Chem. Soc., Perkin Trans. 2 1985, 1865-1868.
74. Bissell, E.; Finger, M. J. Org. Chem. 1959, 24, 1256-1259
75. x will be commercially available from Sigma-Aldrich, Inc., Milwaukee, WI, along with BINOL derivatives -9a and (S)-9a.
76. The amides 8i and 8k-m were made via treatment of the acyl chloride from 3-hydroxy-3-naphthoic acid with the corresponding amines. See the Supporting Information.
77. The phenyl ketones were synthesized by treatment of the lithium anion of 2-methoxynaphthalene with the corresponding aryl Weinreb amides. See the Supporting Information.
78. Nakajima et al. (ref 9d) reported a similar trend: methyl ester, 78% ee; tert-butyl ester, 58% ee.
79. The diphenylphosphine oxide was made by treatment of the lithium anion of 2-methoxynaphthalene with the diphenylphosphonyl chloride. The remaining phosphorous naphthols were made by phosphorylation of 2-naphthol followed by anionic Fries rearrangement. See the Supporting Information.
80. Only two other reports of BINOL-3,3′-phosphine oxides have appeared: (a) Li, J.; Li, W.; Li, Y.; Li, Y.; Yang, S. Org. Prep. Proc. Int. 1995, 27, 685-690. (b) Au-Yeung, T.-L.; Chan, K. Y.; Haynes, R. K.; Williams, I. D.; Yeung, L. L. Tetrahedron Lett. 2001, 57, 457-460.
81. Only two other reports of BINOL-3,3′-phosphine oxides have appeared: (a) Li, J.; Li, W.; Li, Y.; Li, Y.; Yang, S. Org. Prep. Proc. Int. 1995, 27, 685-690. (b) Au-Yeung, T.-L.; Chan, K. Y.; Haynes, R. K.; Williams, I. D.; Yeung, L. L. Tetrahedron Lett. 2001, 57, 457-460.
82. 1H NMR spectra of the diastereomeric solvates formed from (-)-quinine. For examples of analyses using chiral solvating agents, see: (a) Parker, D. Chem. Rev. 1991, 91, 1441-1457. (b) Rosini, C.; Uccello-Barretta, G.; Pini, D.; Abete, C.; Salvadori, P. J. Org. Chem. 1988, 53, 4597-4581.
83. 1H NMR spectra of the diastereomeric solvates formed from (-)-quinine. For examples of analyses using chiral solvating agents, see: (a) Parker, D. Chem. Rev. 1991, 91, 1441-1457. (b) Rosini, C.; Uccello-Barretta, G.; Pini, D.; Abete, C.; Salvadori, P. J. Org. Chem. 1988, 53, 4597-4581.
84. 2, 48 h), 9a was obtained in 26% yield and 84% ee (vs 85% yield and >90% ee for 9a without 9cc). A similar experiment with an analogue of diphenylphosphine oxides 8bb and 9bb (diphenylbutylphosphine oxide) demonstrated that such compounds do not modify the catalyst.
85. The arylsulfonyls were synthesized by treatment of the lithium anion of 2-methoxynaphthalene with the corresponding sulfonyl fluoride. See the Supporting Information.
86. Only a trace of the binaphthyl product and none of the corresponding carbazole were observed, despite prior precedent in the oxidative coupling of this naphthylamine using stoichiometric copper reagents: Vyskočil, S.; Smrčina, M.; Lorenc, M.; Tišlerová, I.; Brooks, R. D.; Kulagowski, J. J.; Langer, V.; Farrugia, L. J.; Kočovský, P. J. Org. Chem. 2001, 66, 1359-1365.
87. Separate attempts to trap an o-keto radical with TEMPO, acrylonitrile, and ethyl phenylcyanoacetate have not succeeded. Another pathway to the aryl iodide is also possible via reductive elimination of an arylcopper iodide. However, the C3 coordinating group in these systems stabilizes the oxygen-bound copper form. We do not see the formation of the aryl halide with the CuCl or CuBr catalysts. While Lipshutz et al. observed a similar trend between CuI and CuCI at low temperature (ref 35a), arylcopper intermediates can give rise to Cl and Br return at the temperatures utilized in our couplings (refs 35b and 35c). (a) Lipshutz, B. H.; Kayser, F.; Siegmann, K. Tetrahedron Lett. 1993, 34, 6693-6696. (b) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1974, 13, 291-305. (c) Piers, E.; McEachern, E. J.; Burns, P. A. Tetrahedron 2000, 56, 2753-2765.
88. Separate attempts to trap an o-keto radical with TEMPO, acrylonitrile, and ethyl phenylcyanoacetate have not succeeded. Another pathway to the aryl iodide is also possible via reductive elimination of an arylcopper iodide. However, the C3 coordinating group in these systems stabilizes the oxygen-bound copper form. We do not see the formation of the aryl halide with the CuCl or CuBr catalysts. While Lipshutz et al. observed a similar trend between CuI and CuCI at low temperature (ref 35a), arylcopper intermediates can give rise to Cl and Br return at the temperatures utilized in our couplings (refs 35b and 35c). (a) Lipshutz, B. H.; Kayser, F.; Siegmann, K. Tetrahedron Lett. 1993, 34, 6693-6696. (b) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1974, 13, 291-305. (c) Piers, E.; McEachern, E. J.; Burns, P. A. Tetrahedron 2000, 56, 2753-2765.
89. Separate attempts to trap an o-keto radical with TEMPO, acrylonitrile, and ethyl phenylcyanoacetate have not succeeded. Another pathway to the aryl iodide is also possible via reductive elimination of an arylcopper iodide. However, the C3 coordinating group in these systems stabilizes the oxygen-bound copper form. We do not see the formation of the aryl halide with the CuCl or CuBr catalysts. While Lipshutz et al. observed a similar trend between CuI and CuCI at low temperature (ref 35a), arylcopper intermediates can give rise to Cl and Br return at the temperatures utilized in our couplings (refs 35b and 35c). (a) Lipshutz, B. H.; Kayser, F.; Siegmann, K. Tetrahedron Lett. 1993, 34, 6693-6696. (b) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1974, 13, 291-305. (c) Piers, E.; McEachern, E. J.; Burns, P. A. Tetrahedron 2000, 56, 2753-2765.
90. Smrčina, M.; Vyskočil, Š.; Maca, B.; Polasek, M.; Claxton, T. A.; Abbott, A. P.; Kočovský, P. J. Org. Chem. 1994, 59, 2156-2163.
91. The formation of the cross-coupled product would also be anticipated if an ionic reaction between a carbocation and neutral molecule was occurring. For a discussion of cationic intermediates in copper phenolic oxidations, see: Baesjou, P. J.; Driessen, W. L.; Challa, G.; Reedijk, J. J. Am. Chem. Soc. 1997, 119, 12590-12594.
92. For prior reports of the asymmetric synthesis of unsymmetric chiral 1,1′-binaphthols via oxidative binaphthol coupling with stoichiometric copper reagents, see refs 9b and 12a (for a discussion of the racemic cases see ref 36 and references therein). For synthesis of chiral 1,1′-binaphthols via intramolecular oxidative coupling of chiral substrates, see: (a) Lipshutz, B. H.; Shin Y.-J. Tetrahedron Lett. 1998, 39, 7017-7020 (unsymmetric 1,1′-binaphthols). (b) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756 (symmetric 1,1′-binaphthols).
93. For prior reports of the asymmetric synthesis of unsymmetric chiral 1,1′-binaphthols via oxidative binaphthol coupling with stoichiometric copper reagents, see refs 9b and 12a (for a discussion of the racemic cases see ref 36 and references therein). For synthesis of chiral 1,1′-binaphthols via intramolecular oxidative coupling of chiral substrates, see: (a) Lipshutz, B. H.; Shin Y.-J. Tetrahedron Lett. 1998, 39, 7017-7020 (unsymmetric 1,1′-binaphthols). (b) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756 (symmetric 1,1′-binaphthols).
94. Faller, J. W.; Grimmond, B. J.; D'Alliessi, D. G. J. Am. Chem. Soc. 2001, 123, 2525-2529 and references therein.
95. 8a is available from 2-hydroxy-3-naphthoic acid (∼$44/kg from Acros or Aldrich) by Fisher esterification and is easily purified by crystallization. The catalyst diamine 7a can also be recovered and reused.
96. 2, MOM group removal, and esterification. (a) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253-2256. (b) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 201-217.
97. 2, MOM group removal, and esterification. (a) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253-2256. (b) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 201-217.
98. Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6-12.
99. Reetz, M. T.; Merk, C.; Mehler, G. Chem. Commun. 1998, 2075-2076.
100. (a) Baret, P.; Beaujolais, V.; Gaude, D.; Coulombeau, C.; Pierre, J.-L. Chem.-Eur. J. 1997, 3, 969-973.
101. (b) Pinkhassik, E.; Stibor, I.; Casnati, A.; Ungaro, R. J. Org. Chem. 1997, 62, 8654-8659.
102. (c) Hodaov, J.; Stibor, I. Collect. Czech. Chem. Commun. 2000, 65, 83-98.
103. Lellek, V.; Stibor, I. J. Mater. Chem. 2000, 10, 1061-1073.
104. Collman, J. P.; Wang, Z.; Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999, 121, 460-461.
105. (a) Kitajima, H.; Aoki, Y.; Ito, K.; Katsuki, T. Chem. Lett. 1995, 1113-1114.
106. (b) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207-217.
107. (c) Kitajima, H.; Ito, K.; Katsuki, T. Chem. Lett. 1996, 343-344.
108. (d) Yang, X.-W.; Sheng, J.-H.; Da, C.-S.; Wang, H.-S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295-296.
109. (e) Yang, X.; Su, W.; Liu, D.; Wang, H.; Shen, J.; Da, C.; Wang, R.; Chan, A. S. C. Tetrahedron 2000, 56, 3511-3516.
110. (a) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028.
111. (b) Casas, J.; Najera, C.; Sansano, J. M.; Gonzalez, J.; Saa, J. M.; Vega, M. Tetrahedron: Asymmetry 2001, 12, 699-702.
112. (c) Casas, J.; Najera, C.; Sansano, J. M.; Saa, J. M. Org. Lett. 2002, 4, 2589-2592.
113. Chen et al. (see ref 9i) have reported a synthesis of 9z via asymmetric biaryl coupling of 8z (61% yield, 76% ee), but the method described here produces the material in the same number of steps with higher yield and selectivity (81% overall yield, >98% ee).
114. For the synthesis of 18 from 9a, see: Hegelson, R. C.; Koga, K.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 3021-3023.
115. (a) Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Sogah, G. D. Y. J. Org. Chem. 1978, 43, 1930-1946.
116. (b) Helgeson, R. C.; Weisman, G. R.; Toner, J. L.; Tarnowski, T. L.; Chao, Y.; Mayer, J. M.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 4928-4941 and references therein.
117. (a) Asakawa, M.; Janssen, H. M.; Meijer, E. W.; Pasini, D.; Stoddart, J. F. Eur. J. Org. Chem. 1998, 983-986.
118. (b) Ashton, P. R.; Heiss, A. M.; Pasini, D.; Raymo, F. R.; Shipway, A. N.; Stoddart, J. F.; Spencer, N. Eur. J. Org. Chem. 1999, 995-1004 and references therein.
119. (a) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641-2642.
120. (b) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 1650-1652.
121. (c) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327-6328.
122. (d) Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 10521-10532.
123. (e) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2000, 48, 1586-1592.
124. (f) Hamashima, Y.; Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2001, 57805-57814.
125. (g) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801-6808.
126. (h) Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784-10785.
127. In other phenol oxidations (which require a free anion) deprotonation is important to the rate: (a) McDonald, F. D.; Hamilton, G. A. J. Am. Chem. Soc. 1973, 95, 7752-7758. (b) Bhattacharjee, M.; Mahanti, M. K. Bull. Soc. Chim. Fr. 1983, I225-I228. For a related discussion, see: (c) Russell, G. A.; Moye, A. J.; Nagpal, K. J. Am. Chem. Soc. 1962, 84, 4154-4155.
128. In other phenol oxidations (which require a free anion) deprotonation is important to the rate: (a) McDonald, F. D.; Hamilton, G. A. J. Am. Chem. Soc. 1973, 95, 7752-7758. (b) Bhattacharjee, M.; Mahanti, M. K. Bull. Soc. Chim. Fr. 1983, I225-I228. For a related discussion, see: (c) Russell, G. A.; Moye, A. J.; Nagpal, K. J. Am. Chem. Soc. 1962, 84, 4154-4155.
129. In other phenol oxidations (which require a free anion) deprotonation is important to the rate: (a) McDonald, F. D.; Hamilton, G. A. J. Am. Chem. Soc. 1973, 95, 7752-7758. (b) Bhattacharjee, M.; Mahanti, M. K. Bull. Soc. Chim. Fr. 1983, I225-I228. For a related discussion, see: (c) Russell, G. A.; Moye, A. J.; Nagpal, K. J. Am. Chem. Soc. 1962, 84, 4154-4155.
130. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
131. 3P=O. Vereshchagina, T. Y.; Vashman, A. A. Zh. Neorg. Khim. 1973, 18, 162-168.
132. 2] = 0.42. See ref 55.
133. An octahedral model that is consistent with the observed stereochemical induction can also be proposed in which two molecules of the substrate 8a and one molecule of the diamine 7a coordinate to a single copper center. However, neither 5- or 6-coordinate geometries were observed in any (out of seven X-ray structures; see ref 21) of the 1,5-diaza-cis-decalin copper complexes. Furthermore, this model would require a Cu(III) to Cu redox cycle, which is not supported by prior investigations of copper-promoted/catalyzed naphthol couplings nor by the low stability of Cu(III) species under the reaction temperatures employed (ambient to 80 °C).
134. Rotation past the smaller enolizing C=O rather than the hydrogens peri to the biaryl bond in 23 is more likely and accounts for the observed product stereochemistry. Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879-881. (b) Meyers, A. I.; Wettlaufer, D. G. J. Am. Chem. Soc. 1984, 106, 1135-1136.
135. Rotation past the smaller enolizing C=O rather than the hydrogens peri to the biaryl bond in 23 is more likely and accounts for the observed product stereochemistry. Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879-881. (b) Meyers, A. I.; Wettlaufer, D. G. J. Am. Chem. Soc. 1984, 106, 1135-1136.
136. In general, we have found that this method produces the compounds in higher yields compared to derivatization of the parent BINOL, and in some cases synthesis from BINOL fails altogether.
137. AM1 calculations with SPARTAN v5.0 (Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612).
138. The order was generated from measures of coordinating ability to Ni(II) [ Munakata, M.; Kitagawa, S.; Miyazima, M. Inorg. Chem. 1986, 24, 1638-1643]
139. or alkynyl iodides [ Brinck, T. J. Phys. Chem. 1997, 101, 3408-3415]
140. and proton affinites [ Bagno, A.; Scorrano, G. J. Am. Chem. Soc. 1988, 110, 4577-4582].