메뉴 건너뛰기




Volumn 63, Issue 8, 1998, Pages 2481-2487

Chiral Pyridines: Optical Resolution of 1-(2-Pyridyl)- and 1-[6-(2,2′-Bipyridyl)]ethanols by Lipase-Catalyzed Enantioselective Acetylation

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0000506063     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971521g     Document Type: Article
Times cited : (80)

References (61)
  • 3
    • 0003643894 scopus 로고
    • John Wiley & Sons: New York
    • Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysts, Products and Catalysts; VCH: Weinhein, 1993; Vol. I. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysts, Ligands; VCH: Weinhein, 1993; Vol. II.
    • (1995) Chiral Auxiliaries and Ligands in Asymmetric Synthesis
    • Seyden-Penne, J.1
  • 4
    • 0003534466 scopus 로고
    • VCH: Weinhein
    • Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysts, Products and Catalysts; VCH: Weinhein, 1993; Vol. I. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysts, Ligands; VCH: Weinhein, 1993; Vol. II.
    • (1993) Handbook of Enantioselective Catalysts, Products and Catalysts , vol.1
    • Brunner, H.1    Zettlmeier, W.2
  • 5
    • 0003394736 scopus 로고
    • VCH: Weinhein
    • Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysts, Products and Catalysts; VCH: Weinhein, 1993; Vol. I. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysts, Ligands; VCH: Weinhein, 1993; Vol. II.
    • (1993) Handbook of Enantioselective Catalysts, Ligands , vol.2
    • Brunner, H.1    Zettlmeier, W.2
  • 6
    • 0001827606 scopus 로고
    • Wilikinson, Sir G., Ed.; Pergamon Press: London
    • Reedijk, J. In Comprehensive Coordination Chemistry; Wilikinson, Sir G., Ed.; Pergamon Press: London, 1987; Vol. 2; p 73. Constable, E. C. Metals and Ligand Reactivity; VCH: Weinheim, 1995.
    • (1987) Comprehensive Coordination Chemistry , vol.2 , pp. 73
    • Reedijk, J.1
  • 7
    • 0004143671 scopus 로고
    • VCH: Weinheim
    • Reedijk, J. In Comprehensive Coordination Chemistry; Wilikinson, Sir G., Ed.; Pergamon Press: London, 1987; Vol. 2; p 73. Constable, E. C. Metals and Ligand Reactivity; VCH: Weinheim, 1995.
    • (1995) Metals and Ligand Reactivity
    • Constable, E.C.1
  • 20
    • 0000323288 scopus 로고
    • Chiral pyridine and bipyridine ligands. Pioneering work was made by the Italian group; see: (a) Botteghi, C.; Caccia, G.; Chelucci, G.; Soccolini, F. J. Org. Chem. 1984, 49, 4290. (b) Botteghi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Organomet. Chem. 1986, 304, 217. (c) Chelucci, G. Tetrahedron: Asymmetry 1995, 6, 811. For recent excellent pyridyl and 2,2′-bipyridyl ligands, see: (d) Bolm, C.; Ewald, M. Tetrahedron Lett. 1990, 37, 5011. (e) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191.
    • (1984) J. Org. Chem. , vol.49 , pp. 4290
    • Botteghi, C.1    Caccia, G.2    Chelucci, G.3    Soccolini, F.4
  • 21
    • 0001274811 scopus 로고
    • Chiral pyridine and bipyridine ligands. Pioneering work was made by the Italian group; see: (a) Botteghi, C.; Caccia, G.; Chelucci, G.; Soccolini, F. J. Org. Chem. 1984, 49, 4290. (b) Botteghi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Organomet. Chem. 1986, 304, 217. (c) Chelucci, G. Tetrahedron: Asymmetry 1995, 6, 811. For recent excellent pyridyl and 2,2′-bipyridyl ligands, see: (d) Bolm, C.; Ewald, M. Tetrahedron Lett. 1990, 37, 5011. (e) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191.
    • (1986) J. Organomet. Chem. , vol.304 , pp. 217
    • Botteghi, C.1    Chelucci, G.2    Chessa, G.3    Delogu, G.4    Gladiali, S.5    Soccolini, F.6
  • 22
    • 0028959981 scopus 로고
    • Chiral pyridine and bipyridine ligands. Pioneering work was made by the Italian group; see: (a) Botteghi, C.; Caccia, G.; Chelucci, G.; Soccolini, F. J. Org. Chem. 1984, 49, 4290. (b) Botteghi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Organomet. Chem. 1986, 304, 217. (c) Chelucci, G. Tetrahedron: Asymmetry 1995, 6, 811. For recent excellent pyridyl and 2,2′-bipyridyl ligands, see: (d) Bolm, C.; Ewald, M. Tetrahedron Lett. 1990, 37, 5011. (e) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 811
    • Chelucci, G.1
  • 23
    • 0025182122 scopus 로고
    • Chiral pyridine and bipyridine ligands. Pioneering work was made by the Italian group; see: (a) Botteghi, C.; Caccia, G.; Chelucci, G.; Soccolini, F. J. Org. Chem. 1984, 49, 4290. (b) Botteghi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Organomet. Chem. 1986, 304, 217. (c) Chelucci, G. Tetrahedron: Asymmetry 1995, 6, 811. For recent excellent pyridyl and 2,2′-bipyridyl ligands, see: (d) Bolm, C.; Ewald, M. Tetrahedron Lett. 1990, 37, 5011. (e) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191.
    • (1990) Tetrahedron Lett. , vol.37 , pp. 5011
    • Bolm, C.1    Ewald, M.2
  • 24
    • 84985653959 scopus 로고
    • Chiral pyridine and bipyridine ligands. Pioneering work was made by the Italian group; see: (a) Botteghi, C.; Caccia, G.; Chelucci, G.; Soccolini, F. J. Org. Chem. 1984, 49, 4290. (b) Botteghi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Organomet. Chem. 1986, 304, 217. (c) Chelucci, G. Tetrahedron: Asymmetry 1995, 6, 811. For recent excellent pyridyl and 2,2′-bipyridyl ligands, see: (d) Bolm, C.; Ewald, M. Tetrahedron Lett. 1990, 37, 5011. (e) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191.
    • (1992) Chem. Ber. , vol.125 , pp. 1191
    • Bolm, C.1    Schlingloff, G.2    Harms, K.3
  • 25
    • 0001279956 scopus 로고
    • For the construction of pyridine and 2,2′-bipyridine ring from chiral cyanides, see: (a) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. (b) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (c) Falorni, M.; Chelucci, G.; Conti, S.; Giacomelli, G. Synthesis 1992, 972. (d) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron 1992, 48, 3653. (e) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 635
    • Gladiali, S.1    Pinna, L.2    Delogu, G.3    De Martin, S.4    Zassinovich, G.5    Mestroni, G.6
  • 26
    • 0026786968 scopus 로고
    • For the construction of pyridine and 2,2′-bipyridine ring from chiral cyanides, see: (a) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. (b) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (c) Falorni, M.; Chelucci, G.; Conti, S.; Giacomelli, G. Synthesis 1992, 972. (d) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron 1992, 48, 3653. (e) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5165
    • Hayoz, P.1    Von Zelewsky, A.2
  • 27
    • 0026737693 scopus 로고
    • For the construction of pyridine and 2,2′-bipyridine ring from chiral cyanides, see: (a) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. (b) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (c) Falorni, M.; Chelucci, G.; Conti, S.; Giacomelli, G. Synthesis 1992, 972. (d) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron 1992, 48, 3653. (e) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
    • (1992) Synthesis , pp. 972
    • Falorni, M.1    Chelucci, G.2    Conti, S.3    Giacomelli, G.4
  • 28
    • 0026572651 scopus 로고
    • For the construction of pyridine and 2,2′-bipyridine ring from chiral cyanides, see: (a) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. (b) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (c) Falorni, M.; Chelucci, G.; Conti, S.; Giacomelli, G. Synthesis 1992, 972. (d) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron 1992, 48, 3653. (e) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
    • (1992) Tetrahedron , vol.48 , pp. 3653
    • Chelucci, G.1    Falorni, M.2    Giacomelli, G.3
  • 29
    • 0028221768 scopus 로고
    • For the construction of pyridine and 2,2′-bipyridine ring from chiral cyanides, see: (a) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. (b) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (c) Falorni, M.; Chelucci, G.; Conti, S.; Giacomelli, G. Synthesis 1992, 972. (d) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron 1992, 48, 3653. (e) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 299
    • Chelucci, G.1    Cabras, M.A.2    Botteghi, C.3    Marchetti, M.4
  • 30
    • 0027411468 scopus 로고
    • For the separation of diastereomers of pyridine and 2,2′-bipyridines, see: (a) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (b) Macedo, E.; Moberg, C. Tetrahedron: Asymmetry, 1995, 6, 549. (c) Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002. (d) Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 411.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2661
    • Ito, K.1    Katsuki, T.2
  • 31
    • 0028967501 scopus 로고
    • For the separation of diastereomers of pyridine and 2,2′-bipyridines, see: (a) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (b) Macedo, E.; Moberg, C. Tetrahedron: Asymmetry, 1995, 6, 549. (c) Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002. (d) Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 411.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 549
    • Macedo, E.1    Moberg, C.2
  • 32
    • 0001447903 scopus 로고    scopus 로고
    • For the separation of diastereomers of pyridine and 2,2′-bipyridines, see: (a) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (b) Macedo, E.; Moberg, C. Tetrahedron: Asymmetry, 1995, 6, 549. (c) Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002. (d) Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 411.
    • (1996) J. Org. Chem. , vol.61 , pp. 8002
    • Zhang, H.1    Xue, F.2    Mak, T.C.W.3    Chan, K.S.4
  • 33
    • 0028217008 scopus 로고
    • For the separation of diastereomers of pyridine and 2,2′-bipyridines, see: (a) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (b) Macedo, E.; Moberg, C. Tetrahedron: Asymmetry, 1995, 6, 549. (c) Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002. (d) Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 411.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 411
    • Ishizaki, M.1    Fujita, K.2    Shimamoto, M.3    Hoshino, O.4
  • 35
    • 0342697384 scopus 로고
    • Reviews for the Corey-Itsuno reduction using oxazaborolidines: (a) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. (b) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475.
    • (1993) Chem. Rev. , vol.93 , pp. 763
    • Deloux, L.1    Srebnik, M.2
  • 36
    • 0026733927 scopus 로고
    • Reviews for the Corey-Itsuno reduction using oxazaborolidines: (a) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. (b) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1475
    • Wallbaum, S.1    Martens, J.2
  • 42
    • 85050327741 scopus 로고
    • Reviews: (a) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1992. (b) Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. (c) Chen. C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. (d) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. (e) Ward, S. C. Chem. Rev. 1990, 90, 1. (f) Enzyme Catalsis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: New York, 1995. (g) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
    • (1989) Top. Stereochem. , vol.19 , pp. 63
    • Sih, C.J.1    Wu, S.-H.2
  • 43
    • 84990106353 scopus 로고
    • Reviews: (a) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1992. (b) Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. (c) Chen. C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. (d) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. (e) Ward, S. C. Chem. Rev. 1990, 90, 1. (f) Enzyme Catalsis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: New York, 1995. (g) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
    • (1989) J. Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 695
    • Chen, C.-S.1    Sih, C.2
  • 44
    • 0642367795 scopus 로고
    • Reviews: (a) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1992. (b) Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. (c) Chen. C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. (d) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. (e) Ward, S. C. Chem. Rev. 1990, 90, 1. (f) Enzyme Catalsis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: New York, 1995. (g) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 114
    • Klibanov, A.M.1
  • 45
    • 0002350894 scopus 로고
    • Reviews: (a) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1992. (b) Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. (c) Chen. C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. (d) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. (e) Ward, S. C. Chem. Rev. 1990, 90, 1. (f) Enzyme Catalsis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: New York, 1995. (g) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
    • (1990) Chem. Rev. , vol.90 , pp. 1
    • Ward, S.C.1
  • 46
    • 0003458664 scopus 로고
    • VCH: New York
    • Reviews: (a) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1992. (b) Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. (c) Chen. C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. (d) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. (e) Ward, S. C. Chem. Rev. 1990, 90, 1. (f) Enzyme Catalsis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: New York, 1995. (g) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
    • (1995) Enzyme Catalsis in Organic Synthesis
    • Drauz, K.1    Waldmann, H.2
  • 47
    • 4243794106 scopus 로고
    • Reviews: (a) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1992. (b) Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. (c) Chen. C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. (d) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. (e) Ward, S. C. Chem. Rev. 1990, 90, 1. (f) Enzyme Catalsis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: New York, 1995. (g) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
    • (1992) Chem. Rev. , vol.92 , pp. 1071
    • Santaniello, E.1    Ferraboschi, P.2    Grisenti, P.3    Manzocchi, A.4
  • 54
    • 85034487207 scopus 로고    scopus 로고
    • The authentic material (S)-2g was prepared according to Bolm's procedure described in ref 12b
    • The authentic material (S)-2g was prepared according to Bolm's procedure described in ref 12b.
  • 57
    • 85034473306 scopus 로고    scopus 로고
    • An appropriate amount of molecular sieves 4A and vinyl acetate should be added for the next batch of the reaction
    • An appropriate amount of molecular sieves 4A and vinyl acetate should be added for the next batch of the reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.