Highly efficient and practical optical resolution of 2-amino-2'-hydroxy- 1,1'-binaphthyl by molecular complexation with N-benzylcinchonidium chloride: A direct transformation to binaphthyl amino phosphine

Chemistry - A European Journal

Volumn 5, Issue 6, 1999, Pages 1734-1737

  Ding, Kuiling ^b   Wang, Yang ^b   Yun, Hongying ^b   Liu, Jinxia ^b   Wu, Yangjie ^b   Terada, Masahiro ^a   Okubo, Yasutaka ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b ZHENGZHOU UNIVERSITY   (China)

Author keywords

Amino alcohols; Biaryls; Molecular recognition; N,P ligands; Optical resolution

Indexed keywords

2 AMINO 2' HYDROXY 1,1' BINAPHTHYL; BINAPHTHYL AMINO PHOSPHINE; NAPHTHALENE DERIVATIVE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; OPTICAL RESOLUTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032976808     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990604)5:6<1734::AID-CHEM1734>3.0.CO;2-G     Document Type: Article

References (40)

1. For general reviews, see: a) H. B. Kagan, in Asymmetric Synthesis; Vol. 5 (E.d.: J. D. Morrison), Academic Press, New York, 1985, pp. 1-35; b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994; c) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993; d) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, Vol. 1 - 2, VCH, New York, 1993.
2. For general reviews, see: a) H. B. Kagan, in Asymmetric Synthesis; Vol. 5 (E.d.: J. D. Morrison), Academic Press, New York, 1985, pp. 1-35; b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994; c) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993; d) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, Vol. 1 - 2, VCH, New York, 1993.
3. For general reviews, see: a) H. B. Kagan, in Asymmetric Synthesis; Vol. 5 (E.d.: J. D. Morrison), Academic Press, New York, 1985, pp. 1-35; b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994; c) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993; d) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, Vol. 1 - 2, VCH, New York, 1993.
4. For general reviews, see: a) H. B. Kagan, in Asymmetric Synthesis; Vol. 5 (E.d.: J. D. Morrison), Academic Press, New York, 1985, pp. 1-35; b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994; c) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993; d) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, Vol. 1 - 2, VCH, New York, 1993.
5. For reviews, see: a) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103. 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; b) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833-856.
6. For reviews, see: a) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103. 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; b) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833-856.
7. For reviews, see: a) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103. 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; b) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833-856.
8. IV complexes of the Schiff hase derivative of 2 show excellen: asymmetric induction in aldol-type reactions, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361. These protocols have been used for the enantioselective synthesis of some bioactive molecules, see: d) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1997, 38, 927-930; e) K. W. Li, J. Wu, W. Xing, J. A. Simon, J. Am. Chem. Soc. 1996, 118, 7237-7238; f) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059. Compound 2 can be also used as a chiral auxiliary for highly enantioselective reactions, see: g) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
9. IV complexes of the Schiff hase derivative of 2 show excellen: asymmetric induction in aldol-type reactions, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361. These protocols have been used for the enantioselective synthesis of some bioactive molecules, see: d) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1997, 38, 927-930; e) K. W. Li, J. Wu, W. Xing, J. A. Simon, J. Am. Chem. Soc. 1996, 118, 7237-7238; f) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059. Compound 2 can be also used as a chiral auxiliary for highly enantioselective reactions, see: g) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
10. IV complexes of the Schiff hase derivative of 2 show excellen: asymmetric induction in aldol-type reactions, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361. These protocols have been used for the enantioselective synthesis of some bioactive molecules, see: d) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1997, 38, 927-930; e) K. W. Li, J. Wu, W. Xing, J. A. Simon, J. Am. Chem. Soc. 1996, 118, 7237-7238; f) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059. Compound 2 can be also used as a chiral auxiliary for highly enantioselective reactions, see: g) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
11. IV complexes of the Schiff hase derivative of 2 show excellen: asymmetric induction in aldol-type reactions, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361. These protocols have been used for the enantioselective synthesis of some bioactive molecules, see: d) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1997, 38, 927-930; e) K. W. Li, J. Wu, W. Xing, J. A. Simon, J. Am. Chem. Soc. 1996, 118, 7237-7238; f) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059. Compound 2 can be also used as a chiral auxiliary for highly enantioselective reactions, see: g) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
12. IV complexes of the Schiff hase derivative of 2 show excellen: asymmetric induction in aldol-type reactions, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361. These protocols have been used for the enantioselective synthesis of some bioactive molecules, see: d) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1997, 38, 927-930; e) K. W. Li, J. Wu, W. Xing, J. A. Simon, J. Am. Chem. Soc. 1996, 118, 7237-7238; f) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059. Compound 2 can be also used as a chiral auxiliary for highly enantioselective reactions, see: g) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
13. IV complexes of the Schiff hase derivative of 2 show excellen: asymmetric induction in aldol-type reactions, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361. These protocols have been used for the enantioselective synthesis of some bioactive molecules, see: d) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1997, 38, 927-930; e) K. W. Li, J. Wu, W. Xing, J. A. Simon, J. Am. Chem. Soc. 1996, 118, 7237-7238; f) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059. Compound 2 can be also used as a chiral auxiliary for highly enantioselective reactions, see: g) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
14. IV complexes of the Schiff hase derivative of 2 show excellen: asymmetric induction in aldol-type reactions, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361. These protocols have been used for the enantioselective synthesis of some bioactive molecules, see: d) E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1997, 38, 927-930; e) K. W. Li, J. Wu, W. Xing, J. A. Simon, J. Am. Chem. Soc. 1996, 118, 7237-7238; f) S. D. Rychnovsky, U. R. Khire, G. Yang, J. Am. Chem. Soc. 1997, 119, 2058-2059. Compound 2 can be also used as a chiral auxiliary for highly enantioselective reactions, see: g) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
15. M. Smrcina, M. Lorenc, V. Hanus, P. Sedmera, P. Kocovsky, J. Org. Chem. 1992, 57, 1917-1920.
16. K. Ding, O. Xu, Y. Wang, J. Liu, Z. Yu, B. Du, Y. Wu, H. Koshima, T. Matsuura, Chem. Commun. 1997, 693-694.
17. H. Mahmoud, Y. Han, B. M. Segal, L. Cai, Tetrahedron: Asymmetry 1998, 9, 2035-2042.
18. For reviews, see: a) F. Toda, Top. Curr. Chem. 1987, 140, 43-69; b) F. Toda, in Advances in Supramolecular Chemistry, Vol. 2 (Ed.: G. W. Gokel), JAI, London, 1992, pp. 41-149; c) G. Kaupp, Angew. Chem. 1994, 106, 768-769; Angew. Chem. Int. Ed. Engl. 1994, 33, 728-729; d) H. Koshima, T. Matsuura, J. Synth. Org. Chem. Jpn. 1998, 56, 268-279 and 466-477; f) Reactivity in Molecular Crystals (Ed.: Y. Ohashi), Kodansha-VCH Tokyo, 1993.
19. For reviews, see: a) F. Toda, Top. Curr. Chem. 1987, 140, 43-69; b) F. Toda, in Advances in Supramolecular Chemistry, Vol. 2 (Ed.: G. W. Gokel), JAI, London, 1992, pp. 41-149; c) G. Kaupp, Angew. Chem. 1994, 106, 768-769; Angew. Chem. Int. Ed. Engl. 1994, 33, 728-729; d) H. Koshima, T. Matsuura, J. Synth. Org. Chem. Jpn. 1998, 56, 268-279 and 466-477; f) Reactivity in Molecular Crystals (Ed.: Y. Ohashi), Kodansha-VCH Tokyo, 1993.
20. For reviews, see: a) F. Toda, Top. Curr. Chem. 1987, 140, 43-69; b) F. Toda, in Advances in Supramolecular Chemistry, Vol. 2 (Ed.: G. W. Gokel), JAI, London, 1992, pp. 41-149; c) G. Kaupp, Angew. Chem. 1994, 106, 768-769; Angew. Chem. Int. Ed. Engl. 1994, 33, 728-729; d) H. Koshima, T. Matsuura, J. Synth. Org. Chem. Jpn. 1998, 56, 268-279 and 466-477; f) Reactivity in Molecular Crystals (Ed.: Y. Ohashi), Kodansha-VCH Tokyo, 1993.
21. For reviews, see: a) F. Toda, Top. Curr. Chem. 1987, 140, 43-69; b) F. Toda, in Advances in Supramolecular Chemistry, Vol. 2 (Ed.: G. W. Gokel), JAI, London, 1992, pp. 41-149; c) G. Kaupp, Angew. Chem. 1994, 106, 768-769; Angew. Chem. Int. Ed. Engl. 1994, 33, 728-729; d) H. Koshima, T. Matsuura, J. Synth. Org. Chem. Jpn. 1998, 56, 268-279 and 466-477; f) Reactivity in Molecular Crystals (Ed.: Y. Ohashi), Kodansha-VCH Tokyo, 1993.
22. For reviews, see: a) F. Toda, Top. Curr. Chem. 1987, 140, 43-69; b) F. Toda, in Advances in Supramolecular Chemistry, Vol. 2 (Ed.: G. W. Gokel), JAI, London, 1992, pp. 41-149; c) G. Kaupp, Angew. Chem. 1994, 106, 768-769; Angew. Chem. Int. Ed. Engl. 1994, 33, 728-729; d) H. Koshima, T. Matsuura, J. Synth. Org. Chem. Jpn. 1998, 56, 268-279 and 466-477; f) Reactivity in Molecular Crystals (Ed.: Y. Ohashi), Kodansha-VCH Tokyo, 1993.
23. For reviews, see: a) F. Toda, Top. Curr. Chem. 1987, 140, 43-69; b) F. Toda, in Advances in Supramolecular Chemistry, Vol. 2 (Ed.: G. W. Gokel), JAI, London, 1992, pp. 41-149; c) G. Kaupp, Angew. Chem. 1994, 106, 768-769; Angew. Chem. Int. Ed. Engl. 1994, 33, 728-729; d) H. Koshima, T. Matsuura, J. Synth. Org. Chem. Jpn. 1998, 56, 268-279 and 466-477; f) Reactivity in Molecular Crystals (Ed.: Y. Ohashi), Kodansha-VCH Tokyo, 1993.
24. a) K. Tanaka, T. Okada, F. Toda, Angew. Chem. 1993, 105, 1266-1267; Angew. Chem. Int. Ed. Engl. 1993, 32, 1147-1148;
25. a) K. Tanaka, T. Okada, F. Toda, Angew. Chem. 1993, 105, 1266-1267; Angew. Chem. Int. Ed. Engl. 1993, 32, 1147-1148;
26. b) F. Toda, K. Tanaka, Z. Stein, I. Goldberg, J. Org. Chem. 1994, 59, 5748-5751;
27. c) F. Toda, K. Tanaka, Chem. Commun. 1997, 1087;
28. d) D. W. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991-7994;
29. e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123-2126.
30. 2 (706.32): C 78.22, H 6.28, N 5.95%; found: C 78.15, H 6.30, N 6.04%.
31. a) K. Tanaka, K. Tamura, F. Toda, J. Chem. Soc. Perkin Trans. 2, 1995, 1571-1572;
32. b) F. Toda, K. Tanaka, H. Sawada, J. Chem. Soc. Perkin Trans. 1 1995, 3065-3066.
33. max = 55.0) were used for the solution of the structure. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included but not refined. R = 0.075, wR = 0.092. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-102753. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
34. In a similar manner, racemic BINOL can be effectively resolved by using 0.5 equiv of N-benzylcinchonidium chloride (3) as resolving agent. The BINOL included in the molecular crystal was found to have an (R)-(+) configuration.
35. A. W. Rastou, D. N. Eggenberger, J. Am. Chem. Soc. 1947, 69, 2095-2097.
36. 2/dppp: d) G. Martorell, X. Garcias, M. Janura, J. M. Saa, J. Org. Chem. 1998, 63, 3463-3467: e) G. Bringmann, A. Wuzik, C. Vedder, M. Pfeiffer, D. Stalke, Chem. Commum. 1998, 1211-1212.
37. 2/dppp: d) G. Martorell, X. Garcias, M. Janura, J. M. Saa, J. Org. Chem. 1998, 63, 3463-3467: e) G. Bringmann, A. Wuzik, C. Vedder, M. Pfeiffer, D. Stalke, Chem. Commum. 1998, 1211-1212.
38. 2/dppp: d) G. Martorell, X. Garcias, M. Janura, J. M. Saa, J. Org. Chem. 1998, 63, 3463-3467: e) G. Bringmann, A. Wuzik, C. Vedder, M. Pfeiffer, D. Stalke, Chem. Commum. 1998, 1211-1212.
39. 2/dppp: d) G. Martorell, X. Garcias, M. Janura, J. M. Saa, J. Org. Chem. 1998, 63, 3463-3467: e) G. Bringmann, A. Wuzik, C. Vedder, M. Pfeiffer, D. Stalke, Chem. Commum. 1998, 1211-1212.
40. 2/dppp: d) G. Martorell, X. Garcias, M. Janura, J. M. Saa, J. Org. Chem. 1998, 63, 3463-3467: e) G. Bringmann, A. Wuzik, C. Vedder, M. Pfeiffer, D. Stalke, Chem. Commum. 1998, 1211-1212.