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Volumn 37, Issue 42, 1996, Pages 7623-7626

Catalytic racemisation of alcohols: Applications of enzymatic resolution reactions

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

EID: 0030583519     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01677-2     Document Type: Article
Times cited : (245)

References (17)
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    • (1995) Enzyme Catalysis in Organic Synthesis , vol.1 , pp. 165-343
    • Drauz, K.1    Waldman, H.2
  • 2
    • 0029125707 scopus 로고
    • 1. Enzyme Catalysis in Organic Synthesis, ed. Drauz, K.; Waldman, H. VCH, Weinheim, 1995, vol. 1, 165-343. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry, 1995, 6, 2385-2394. Burgess, K.; Jennings, L.D. J. Am. Chem. Soc., 1991, 113, 6129-6139.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2385-2394
    • Naemura, K.1    Fukuda, R.2    Murata, M.3    Konishi, M.4    Hirose, K.5    Tobe, Y.6
  • 3
    • 0001364513 scopus 로고
    • 1. Enzyme Catalysis in Organic Synthesis, ed. Drauz, K.; Waldman, H. VCH, Weinheim, 1995, vol. 1, 165-343. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry, 1995, 6, 2385-2394. Burgess, K.; Jennings, L.D. J. Am. Chem. Soc., 1991, 113, 6129-6139.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6129-6139
    • Burgess, K.1    Jennings, L.D.2
  • 4
    • 0029968623 scopus 로고    scopus 로고
    • 2. Recently we have shown that the palladium catalysed racemisation of suitable allylic acetates is possible in the presence of Pseudomonas fluorescens Lipase. Allen, J.V.; Williams, J.M.J. Tetrahedron Lett., 1996, 37, 1859-1862.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1859-1862
    • Allen, J.V.1    Williams, J.M.J.2
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    • 7. Evans, D.A.; Nelson, S.G.; Gagné, M.R.; Muci, A.R. J. Am. Chem. Soc., 1993, 115, 9800-9801. Lebrun, A.; Namy, J.-L.; Kagan, H.B.; Tetrahedron Lett., 1991, 32, 2355-2358. Zassinovich, G.; Mestroni, G. Chem. Rev., 1992, 92, 1051-1069.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9800-9801
    • Evans, D.A.1    Nelson, S.G.2    Gagné, M.R.3    Muci, A.R.4
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    • 7. Evans, D.A.; Nelson, S.G.; Gagné, M.R.; Muci, A.R. J. Am. Chem. Soc., 1993, 115, 9800-9801. Lebrun, A.; Namy, J.-L.; Kagan, H.B.; Tetrahedron Lett., 1991, 32, 2355-2358. Zassinovich, G.; Mestroni, G. Chem. Rev., 1992, 92, 1051-1069.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2355-2358
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    • 7. Evans, D.A.; Nelson, S.G.; Gagné, M.R.; Muci, A.R. J. Am. Chem. Soc., 1993, 115, 9800-9801. Lebrun, A.; Namy, J.-L.; Kagan, H.B.; Tetrahedron Lett., 1991, 32, 2355-2358. Zassinovich, G.; Mestroni, G. Chem. Rev., 1992, 92, 1051-1069.
    • (1992) Chem. Rev. , vol.92 , pp. 1051-1069
    • Zassinovich, G.1    Mestroni, G.2
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    • 9. Zassinovich, G.; Mestroni, G. J. Mol. Catal., 1987, 42, 81-90. Müller, D; Umbricht, G; Weber, B; Pfaltz, A. Helv. Chim. Acta, 1991, 74, 232-240.
    • (1987) J. Mol. Catal. , vol.42 , pp. 81-90
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    • ed. Trost, B.M.; Fleming, I. Pergamon, Oxford
    • 11. Kellogg, R.M. in Comprehensive Organic Synthesis ed. Trost, B.M.; Fleming, I. Pergamon, Oxford, 1991, vol. 8, 88-91.
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    • Kellogg, R.M.1
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    • The use of the higher temperature (up to 80 °C) was not responsible for the lower selectivities. Thus, the PFL catalysed acylation of phenethyl alcohol 1 at 80 °C in the absence of any co-catalyst afforded the product in 95% ee at 43% conversion after 24 hours
    • 12. The use of the higher temperature (up to 80 °C) was not responsible for the lower selectivities. Thus, the PFL catalysed acylation of phenethyl alcohol 1 at 80 °C in the absence of any co-catalyst afforded the product in 95% ee at 43% conversion after 24 hours.


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