메뉴 건너뛰기




Volumn 13, Issue 24, 2002, Pages 2679-2687

Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 FURYL)BUT 3 EN 1 OL; 1 (2 PYRIDYL)BUT 3 EN 1 OL; 1 (2 PYRIDYL)BUT 3 YN 1 OL; 1 (2 THIENYL)BUT 3 EN 1 OL; 1 (3 PYRIDYL)BUT 3 EN 1 OL; 1 (3 PYRIDYL)BUT 3 YN 1 OL; 1 (3 PYRIDYL)BUTA 2,3 DIEN 1 OL; 1 (4 PYRIDYL)BUT 3 EN 1 OL; 3 (1 HYDROXYBUT 3 EN 1 YL)CHROMEN 4 ONE; ALCOHOL DERIVATIVE; HOMOALLYLIC ALCOHOL; HOMOPROPARGYLIC ALCOHOL; UNCLASSIFIED DRUG;

EID: 0037049384     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00743-7     Document Type: Article
Times cited : (29)

References (119)
  • 2
    • 0003441482 scopus 로고    scopus 로고
    • John Wiley & Sons: Chichester; Chapter 4
    • Nicalaou K.C., Roschanger F., Vourloumis D. Angew. Chem., Int. Ed. Engl. 37:1998;2104. and references cited therein Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: Chichester, 1997; Chapter 4.
    • (1997) Palladium Reagents and Catalysts
    • Tsuji, J.1
  • 30
    • 84992649988 scopus 로고    scopus 로고
    • Chiu, P.; Lautens, M. Stereoselective Heterocyclic Synthesis; Metz, P., Ed.; Springer-Verlag: Berlin Heidelberg, 1999; Chapter 1
    • Chiu, P.; Lautens, M. Stereoselective Heterocyclic Synthesis; Metz, P., Ed.; Springer-Verlag: Berlin Heidelberg, 1999; Chapter 1.
  • 32
    • 0012051476 scopus 로고    scopus 로고
    • Katritzky, A. R., Ed.; Academic Press: California, Chapter 2
    • Pozharskii A.F., Soldatenkov A.T., Katritzky A.R. Heterocycles in Life and Society. 1997;John Wiley & Sons, Chichester, Moreno-Manas, M.; Pleixats, R. Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: California, 1996; Vol. 66, Chapter 2.
    • (1996) Advances in Heterocyclic Chemistry , pp. 66
    • Moreno-Manas, M.1    Pleixats, R.2
  • 38
    • 0003913629 scopus 로고    scopus 로고
    • Otera, J., Ed.; Wiley-VCH; Weinheim; Chapter 10;
    • For recent reviews for allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000; Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; © Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
    • (2000) Modern Carbonyl Chemistry
    • Denmark, S.E.1    Almstead, N.G.2
  • 39
    • 4243893500 scopus 로고
    • For recent reviews for allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000; Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; © Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 40
    • 0000530692 scopus 로고
    • For recent reviews for allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000; Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; © Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6619
    • Evans, D.A.1    Dart, M.J.2    Duffy, J.L.3    Yang, M.G.4    Livingston, A.B.5
  • 41
    • 0001057466 scopus 로고
    • For recent reviews for allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000; Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; © Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 265
    • Keck, G.E.1    Boden, E.P.2
  • 42
    • 0000725791 scopus 로고
    • For recent reviews for allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000; Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; © Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3927
    • Keck, G.E.1    Abbott, D.E.2    Boden, E.P.3    Enholm, E.J.4
  • 43
    • 0001258383 scopus 로고
    • For recent reviews for allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000; Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; © Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 139
    • Keck, G.E.1    Abbott, D.E.2    Wiley, M.R.3
  • 44
    • 33751158182 scopus 로고
    • For recent reviews for allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000; Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; © Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
    • (1994) J. Org. Chem. , vol.59 , pp. 7889
    • Keck, G.E.1    Savin, K.A.2    Cressman, E.N.K.3    Abbott, D.E.4
  • 60
    • 0012021036 scopus 로고    scopus 로고
    • Some representative reviews and articles for enantioselective allylation are: (a) Marshall, J. A. Chemtracts-Organic Chemistry 1996, 9, 280; (b) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gaz. Chim. Ital. 1997, 127, 247; © Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363l; (d) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561.
    • (1996) Chemtracts-Organic Chemistry , vol.9 , pp. 280
    • Marshall, J.A.1
  • 61
    • 0001604863 scopus 로고    scopus 로고
    • Some representative reviews and articles for enantioselective allylation are: (a) Marshall, J. A. Chemtracts-Organic Chemistry 1996, 9, 280; (b) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gaz. Chim. Ital. 1997, 127, 247; © Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363l; (d) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561.
    • (1997) Gaz. Chim. Ital. , vol.127 , pp. 247
    • Cozzi, P.G.1    Tagliavini, E.2    Umani-Ronchi, A.3
  • 62
    • 0030472831 scopus 로고    scopus 로고
    • Some representative reviews and articles for enantioselective allylation are: (a) Marshall, J. A. Chemtracts-Organic Chemistry 1996, 9, 280; (b) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gaz. Chim. Ital. 1997, 127, 247; © Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363l; (d) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2363
    • Gauthier, D.R.1    Carreira, E.M.2
  • 63
    • 85022536996 scopus 로고
    • Some representative reviews and articles for enantioselective allylation are: (a) Marshall, J. A. Chemtracts-Organic Chemistry 1996, 9, 280; (b) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gaz. Chim. Ital. 1997, 127, 247; © Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363l; (d) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561.
    • (1991) Synlett , pp. 561
    • Furuta, K.1    Mouri, M.2    Yamamoto, H.3
  • 68
    • 0000677232 scopus 로고
    • For a review, see: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; © Cintas, P. Synlett 1995, 1087;
    • (1993) J. Chem. Rev. , vol.93 , pp. 2023
    • Li, C.1
  • 69
    • 0028430856 scopus 로고
    • For a review, see: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; © Cintas, P. Synlett 1995, 1087;
    • (1994) Can. J. Chem. , vol.72 , pp. 1181
    • Chan, T.H.1    Li, C.J.2    Lee, M.C.3    Wei, Z.Y.4
  • 70
    • 0037571395 scopus 로고
    • For a review, see: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; © Cintas, P. Synlett 1995, 1087;
    • (1995) Synlett , pp. 1087
    • Cintas, P.1
  • 71
    • 0001310676 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3228
    • Chan, T.H.1    Yang, Y.2
  • 72
    • 33845278851 scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1988) J. Org. Chem. , vol.53 , pp. 1831
    • Araki, S.1    Ito, H.2    Butsugan, Y.3
  • 73
    • 0029873889 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1917
    • Paquette, L.A.1    Lobben, P.C.2
  • 74
    • 0029933487 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1931
    • Paquette, L.A.1    Mitzel, T.M.2
  • 75
    • 0000125198 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1997) J. Org. Chem. , vol.62 , pp. 2318
    • Fujiwara, N.1    Yamamoto, Y.2
  • 76
    • 0000126518 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1997) J. Org. Chem. , vol.62 , pp. 4293
    • Paquette, L.A.1    Mitzel, T.M.2    Isaac, M.B.3    Crasto, C.F.4    Schomer, W.W.5
  • 77
    • 0033534707 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1999) J. Org. Chem. , vol.64 , pp. 172
    • Hirashita, T.1    Kamei, T.2    Horie, T.3    Yamamura, H.4    Kawai, M.5    Araki, S.6
  • 78
    • 0033534542 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1999) J. Org. Chem. , vol.64 , pp. 217
    • Paquette, L.A.1    Rothaar, R.R.2
  • 79
    • 0033543497 scopus 로고    scopus 로고
    • (d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org. Chem. 1999, 64, 217; (m) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
    • (1999) Tetrahedron , vol.55 , pp. 11149
    • Li, C.J.1    Chan, T.H.2
  • 85
    • 0041152088 scopus 로고    scopus 로고
    • Carrea G., Riva S. Angew. Chem., Int. Ed. 39:2000;2226 Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 1999.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2226
    • Carrea, G.1    Riva, S.2
  • 86
    • 0003993814 scopus 로고    scopus 로고
    • Patel, R. N., Ed.; Marcel Dekker: New York
    • Carrea G., Riva S. Angew. Chem., Int. Ed. 39:2000;2226 Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 1999.
    • (1999) Stereoselective Biocatalysis
  • 87
    • 0035498331 scopus 로고    scopus 로고
    • Kadereit D., Waldmann H. Chem. Rev. 101:2001;3367 Enzymatic Reactions in Organic Media, Koskinen, A. M. P.; Klibanov, A. M., Eds.; Blackie Academic & Professional: Glasgow, 1996 Hydrolases in Organic Synthesis, Bornscheuer, U. T.; Kazlauskas, R. J., Eds.; Wiley-VCH: Weinheim, 1999.
    • (2001) Chem. Rev. , vol.101 , pp. 3367
    • Kadereit, D.1    Waldmann, H.2
  • 88
    • 0035498331 scopus 로고    scopus 로고
    • Blackie Academic & Professional: Glasgow
    • Kadereit D., Waldmann H. Chem. Rev. 101:2001;3367 Enzymatic Reactions in Organic Media, Koskinen, A. M. P.; Klibanov, A. M., Eds.; Blackie Academic & Professional: Glasgow, 1996 Hydrolases in Organic Synthesis, Bornscheuer, U. T.; Kazlauskas, R. J., Eds.; Wiley-VCH: Weinheim, 1999.
    • (1996) Enzymatic Reactions in Organic Media
    • Koskinen, A.M.P.1    Klibanov, A.M.2
  • 89
    • 0035498331 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim
    • Kadereit D., Waldmann H. Chem. Rev. 101:2001;3367 Enzymatic Reactions in Organic Media, Koskinen, A. M. P.; Klibanov, A. M., Eds.; Blackie Academic & Professional: Glasgow, 1996 Hydrolases in Organic Synthesis, Bornscheuer, U. T.; Kazlauskas, R. J., Eds.; Wiley-VCH: Weinheim, 1999.
    • (1999) Hydrolases in Organic Synthesis
    • Bornscheuer, U.T.1    Kazlauskas, R.J.2
  • 93
    • 0033615512 scopus 로고    scopus 로고
    • For synthesis of non-racemic homopropargylic alcohols, see: (a) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214; (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812.
    • (1999) J. Org. Chem. , vol.64 , pp. 8214
    • Marshall, J.A.1    Grant, C.M.2
  • 94
    • 0000536832 scopus 로고    scopus 로고
    • For synthesis of non-racemic homopropargylic alcohols, see: (a) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214; (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812.
    • (1998) J. Org. Chem. , vol.63 , pp. 3812
    • Marshall, J.A.1    Adams, N.D.2
  • 97
    • 0030590974 scopus 로고    scopus 로고
    • For enzymatic resolution of racemic homoallylic alcohols, see: (a) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253; (b) Adam, W.; Saha-Moller, C. R.; Schmid, K. S. Tetrahedron: Asymmetry 1999, 10, 315; © Bierstedt, A.; Stolting, J.; Frohlich, R.; Metz, P. Tetrahedron: Asymmetry 2001, 12, 3399; (d) Uenishi, J.; Hiraoka, T.; Hata, S.; Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481; (e) Morgan, B.; Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992, 57, 3231; (f) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9253
    • Master, H.E.1    Newadkar, R.V.2    Rane, R.A.3    Kumar, A.4
  • 98
    • 0344527959 scopus 로고    scopus 로고
    • For enzymatic resolution of racemic homoallylic alcohols, see: (a) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253; (b) Adam, W.; Saha-Moller, C. R.; Schmid, K. S. Tetrahedron: Asymmetry 1999, 10, 315; © Bierstedt, A.; Stolting, J.; Frohlich, R.; Metz, P. Tetrahedron: Asymmetry 2001, 12, 3399; (d) Uenishi, J.; Hiraoka, T.; Hata, S.; Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481; (e) Morgan, B.; Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992, 57, 3231; (f) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 315
    • Adam, W.1    Saha-Moller, C.R.2    Schmid, K.S.3
  • 99
    • 0037148428 scopus 로고    scopus 로고
    • For enzymatic resolution of racemic homoallylic alcohols, see: (a) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253; (b) Adam, W.; Saha-Moller, C. R.; Schmid, K. S. Tetrahedron: Asymmetry 1999, 10, 315; © Bierstedt, A.; Stolting, J.; Frohlich, R.; Metz, P. Tetrahedron: Asymmetry 2001, 12, 3399; (d) Uenishi, J.; Hiraoka, T.; Hata, S.; Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481; (e) Morgan, B.; Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992, 57, 3231; (f) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3399
    • Bierstedt, A.1    Stolting, J.2    Frohlich, R.3    Metz, P.4
  • 100
    • 0000506063 scopus 로고    scopus 로고
    • For enzymatic resolution of racemic homoallylic alcohols, see: (a) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253; (b) Adam, W.; Saha-Moller, C. R.; Schmid, K. S. Tetrahedron: Asymmetry 1999, 10, 315; © Bierstedt, A.; Stolting, J.; Frohlich, R.; Metz, P. Tetrahedron: Asymmetry 2001, 12, 3399; (d) Uenishi, J.; Hiraoka, T.; Hata, S.; Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481; (e) Morgan, B.; Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992, 57, 3231; (f) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018.
    • (1998) J. Org. Chem. , vol.63 , pp. 2481
    • Uenishi, J.1    Hiraoka, T.2    Hata, S.3    Nishiwaki, K.4    Yonemitsu, O.5    Nakamura, K.6    Tsukube, H.7
  • 101
    • 0000123148 scopus 로고
    • For enzymatic resolution of racemic homoallylic alcohols, see: (a) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253; (b) Adam, W.; Saha-Moller, C. R.; Schmid, K. S. Tetrahedron: Asymmetry 1999, 10, 315; © Bierstedt, A.; Stolting, J.; Frohlich, R.; Metz, P. Tetrahedron: Asymmetry 2001, 12, 3399; (d) Uenishi, J.; Hiraoka, T.; Hata, S.; Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481; (e) Morgan, B.; Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992, 57, 3231; (f) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018.
    • (1992) J. Org. Chem. , vol.57 , pp. 3231
    • Morgan, B.1    Oehlschlager, A.C.2    Stokes, T.M.3
  • 102
    • 0027973117 scopus 로고
    • For enzymatic resolution of racemic homoallylic alcohols, see: (a) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253; (b) Adam, W.; Saha-Moller, C. R.; Schmid, K. S. Tetrahedron: Asymmetry 1999, 10, 315; © Bierstedt, A.; Stolting, J.; Frohlich, R.; Metz, P. Tetrahedron: Asymmetry 2001, 12, 3399; (d) Uenishi, J.; Hiraoka, T.; Hata, S.; Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481; (e) Morgan, B.; Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992, 57, 3231; (f) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018.
    • (1994) J. Org. Chem. , vol.59 , pp. 6018
    • Pai, Y.-C.1    Fang, J.-M.2    Wu, S.-H.3
  • 111
    • 84992537467 scopus 로고    scopus 로고
    • 3 solution
    • 3 solution.
  • 119
    • 84992566730 scopus 로고    scopus 로고
    • D could not recorded as there were wide fluctuations in the value given by polarimeter (when a solution of (R)-6b or (S)-4b was used) and no stable value could be obtained
    • D could not recorded as there were wide fluctuations in the value given by polarimeter (when a solution of (R)-6b or (S)-4b was used) and no stable value could be obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.