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Volumn 70, Issue 2, 1997, Pages 483-491

Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on Pichia farinosa-Catalyzed anti-Prelog-Rule Reduction as the Key Step

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EID: 0000431467     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.483     Document Type: Article
Times cited : (35)

References (120)
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    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
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    • Crumbie, R.L.1    Deol, B.S.2    Nemorin, J.E.3    Ridley, D.D.4
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    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
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    • Ghiringhelli, D.1
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    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
    • (1985) Tetrahedron Lett. , vol.26 , pp. 771
    • Fujisawa, T.1    Itoh, T.2    Nakai, M.3    Sato, T.4
  • 5
    • 0017822478 scopus 로고    scopus 로고
    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
    • Synthesis , vol.1987 , pp. 570
    • Tanikaga, R.1    Hosoya, K.2    Kaji, A.3
  • 6
    • 0017822478 scopus 로고    scopus 로고
    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
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    • Fujisawa, T.1    Fujimura, A.2    Sato, T.3
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    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2197
    • Sato, T.1    Hanayama, K.2    Fujisawa, T.3
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    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 3513
    • Chikashita, H.1    Ohkawa, K.2    Itoh, K.3
  • 9
    • 0017822478 scopus 로고    scopus 로고
    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
    • Chem. Lett. , vol.1989 , pp. 1755
    • Noda, Y.1    Kikuchi, M.2
  • 10
    • 0017822478 scopus 로고    scopus 로고
    • S. Iriuchijima and N. Kojima, Agric. Biol. Chem., 42, 451 (1978); R. L. Crumbie, B. S. Deol, J. E. Nemorin, and D. D. Ridley, Aust. J. Chem., 31, 1965 (1978); D. Ghiringhelli, Tetrahedron Lett., 24, 287 (1983); T. Fujisawa, T. Itoh, M. Nakai, and T. Sato, Tetrahedron Lett., 26, 771 (1985); R. Tanikaga, K. Hosoya, and A. Kaji, Synthesis, 1987, 570; T. Fujisawa, A. Fujimura, and T. Sato, Bull. Chem. Soc. Jpn., 61, 1273 (1988); T. Sato, K. Hanayama, and T. Fujisawa, Tetrahedron Lett., 29, 2197 (1988); H. Chikashita, K. Ohkawa, and K. Itoh, Bull. Chem. Soc. Jpn., 62, 3513 (1989); Y. Noda and M. Kikuchi, Chem. Lett., 1989, 1755; R. Bernardi and D. Ghiringhelli, Synthesis, 1989, 938; T. Takemura, Y. Hosoya, and N. Mori, Can. J. Chem., 68, 523 (1990); T. Fujisawa, K. Yamanaka, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 32, 399 (1991); T. Fujisawa, B. I. Mobele, and M. Shimidzu, Tetrahedron Lett., 32, 7055 (1991); T. Fujisawa, B. I. Mobele, and M. Shimizu, Tetrahedron Lett., 33, 5567 (1992); K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri, and H. Yoda, Tetrahedron: Asymmetry, 3, 1399 (1992); C. A. M. Afonso, M. T. Barros, L. S. Godinho, and C. D. Maycock, Tetrahedron, 49, 4283 (1993); H. Nakamura, K. Fujimaki, O. Sampei, and A. Murai, Tetrahedron Lett., 34, 8481 (1993); H. Matsumae, H. Douno, S. Yamada, T. Nishida, Y. Ozaki, T. Shibatani, and T. Tosa, J. Ferment. Bioeng., 79, 28 (1995); A. Svatos, Z. Hunková, V. Kren, M. Hoskovec, D. Saman, I. Lalterová, J. Vrkoc, and B. Koutek, Tetrahedron: Asymmetry, 7, 1285 (1996); see also a review: T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).
    • Synthesis , vol.1989 , pp. 938
    • Bernardi, R.1    Ghiringhelli, D.2
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