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Volumn 9, Issue , 2012, Pages 129-146

9.7 Industrial Applications of the Jacobsen Hydrolytic Kinetic Resolution Technology

Author keywords

1,2 diols; Asymmetric catalysis; Chiral (salen) metal catalysts; Chiral building blocks; Cooperative catalysis; Epoxides; Hydrolytic kinetic resolution; Industrial processes; Oligomeric catalysts

Indexed keywords


EID: 84902416890     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-095167-6.00910-1     Document Type: Chapter
Times cited : (8)

References (65)
  • 1
    • 0000308108 scopus 로고
    • Kinetic Resolution
    • For the leading reference on kinetic resolutions, see: (a), Wiley, New York, pp 249-330. See also the discussion in reference 4.
    • Kagan H.B., Fiaud J.C. Kinetic Resolution. Topics in Stereochemistry 1987, Vol. 14. For the leading reference on kinetic resolutions, see: (a), Wiley, New York, pp 249-330. See also the discussion in reference 4.
    • (1987) Topics in Stereochemistry , vol.14
    • Kagan, H.B.1    Fiaud, J.C.2
  • 2
    • 84902434204 scopus 로고    scopus 로고
    • For reviews of chiral (salen)-metal complexes and the reactions catalyzed by them
    • see: (a) Larrow, J. F.; Jacobsen, E. N. Asymmetric Processes Catalyzed by Chiral (Salen)Metal Complexes. In Topics in Organometallic Chemistry; Larsen, R. D., Ed.; Springer-Verlag: Berlin
    • For reviews of chiral (salen)-metal complexes and the reactions catalyzed by them, see: (a) Larrow, J. F.; Jacobsen, E. N. Asymmetric Processes Catalyzed by Chiral (Salen)Metal Complexes. In Topics in Organometallic Chemistry; Larsen, R. D., Ed.; Springer-Verlag: Berlin, 2004, Vol. 6; pp 123-152.
    • (2004) , vol.6 , pp. 123-152
  • 5
    • 84886382946 scopus 로고    scopus 로고
    • Asymmetry in the Plant: Concepts and Principles for the Scale-Up of Asymmetric Organic Reactions.
    • Comprehensive Chirality; Hughes, D. L., Ed.; Elsevier: London, 2012, Vol. 9; Chapter 9.2.
    • Federsel, H.-J. Asymmetry in the Plant: Concepts and Principles for the Scale-Up of Asymmetric Organic Reactions. In Comprehensive Chirality; Hughes, D. L., Ed.; Elsevier: London, 2012, Vol. 9; Chapter 9.2.
    • Federsel, H.-J.1
  • 6
    • 0034697497 scopus 로고    scopus 로고
    • Wiley-VCH, Weinheim, H.-U. Blaser, E. Schmidt (Eds.)
    • Asymmetric Catalysis on Industrial Scale 2004, Wiley-VCH, Weinheim. H.-U. Blaser, E. Schmidt (Eds.).
    • (2004) Asymmetric Catalysis on Industrial Scale
  • 11
    • 84902428796 scopus 로고    scopus 로고
    • Innovations Pharmaceut.
    • 116
    • DiMare, M. Innovations Pharmaceut. Technol. 2002, 2(10), 116, 118-121.
    • (2002) Technol. , vol.2 , Issue.10 , pp. 118-121
    • DiMare, M.1
  • 22
    • 77950515233 scopus 로고    scopus 로고
    • For a recent review of cooperative catalysis by metallosalen complexes, see:
    • Haak R.M., Wezenberg S.J., Kliej A.W. Chem. Commun. 2010, 46(16):2713-2723. For a recent review of cooperative catalysis by metallosalen complexes, see:.
    • (2010) Chem. Commun. , vol.46 , Issue.16 , pp. 2713-2723
    • Haak, R.M.1    Wezenberg, S.J.2    Kliej, A.W.3
  • 24
    • 67849097720 scopus 로고    scopus 로고
    • For a solution-state study of several (salen)Co(III) complexes and potential implications to the conformation of 1b in the selectivity-determining step, see:
    • Kemper S., Hrobárik P., Kaupp M., Schlörer N.E. J. Am. Chem. Soc. 2009, 131(12):4172-4173. For a solution-state study of several (salen)Co(III) complexes and potential implications to the conformation of 1b in the selectivity-determining step, see:.
    • (2009) J. Am. Chem. Soc. , vol.131 , Issue.12 , pp. 4172-4173
    • Kemper, S.1    Hrobárik, P.2    Kaupp, M.3    Schlörer, N.E.4
  • 27
    • 85026872509 scopus 로고    scopus 로고
    • (Coll. Vol. 11, 2009, pp 157-163). See also a discussion in reference 2a (pp 132-134).
    • Stevenson C.P., Nielsen L.P.C., Jacobsen E.N., et al. Org. Synth. 2006, 83:162-169. (Coll. Vol. 11, 2009, pp 157-163). See also a discussion in reference 2a (pp 132-134).
    • (2006) Org. Synth. , vol.83 , pp. 162-169
    • Stevenson, C.P.1    Nielsen, L.P.C.2    Jacobsen, E.N.3
  • 29
    • 0036569687 scopus 로고    scopus 로고
    • For evidence of enantiomer discrimination through selective binding to chiral (salen)metal complexes, see:
    • Bobb R., Alhakimi G., Studnicki L., Lough A., Chin J. J. Am. Chem. Soc. 2002, 124(17):4544-4545. For evidence of enantiomer discrimination through selective binding to chiral (salen)metal complexes, see:.
    • (2002) J. Am. Chem. Soc. , vol.124 , Issue.17 , pp. 4544-4545
    • Bobb, R.1    Alhakimi, G.2    Studnicki, L.3    Lough, A.4    Chin, J.5
  • 32
    • 19444382133 scopus 로고    scopus 로고
    • Industrialization Studies of the Jacobsen Hydrolytic Kinetic Resolution of Epichlorohydrin
    • Wiley-VCH, Weinheim, Chapter II-2, H.-U. Blaser, E. Schmidt (Eds.)
    • Aouni L., Hemberger K.E., Jasmin S., et al. Industrialization Studies of the Jacobsen Hydrolytic Kinetic Resolution of Epichlorohydrin. Asymmetric Catalysis on Industrial Scale 2004, 165-199. Wiley-VCH, Weinheim, Chapter II-2. H.-U. Blaser, E. Schmidt (Eds.).
    • (2004) Asymmetric Catalysis on Industrial Scale , pp. 165-199
    • Aouni, L.1    Hemberger, K.E.2    Jasmin, S.3
  • 33
    • 84902427009 scopus 로고    scopus 로고
    • (Rhodia Pharma Solutions) Active Catalysts for Stereoselective Ring-Opening Reactions.
    • US Patent 6,781,006
    • Larrow, J. F.; Hemberger, K. E.; Kabir, H.; Morel, P. (Rhodia Pharma Solutions) Active Catalysts for Stereoselective Ring-Opening Reactions. US Patent 6,781,006, 2004.
    • (2004)
    • Larrow, J.F.1    Hemberger, K.E.2    Kabir, H.3    Morel, P.4
  • 37
    • 77149132445 scopus 로고    scopus 로고
    • For recent reports of other building blocks derived from PO, see:
    • Anderson K.R., Atkinson S.L.G., Fujiwara T., et al. Org. Process Res. Dev. 2010, 14(1):58-71. For recent reports of other building blocks derived from PO, see:.
    • (2010) Org. Process Res. Dev. , vol.14 , Issue.1 , pp. 58-71
    • Anderson, K.R.1    Atkinson, S.L.G.2    Fujiwara, T.3
  • 40
    • 4243227950 scopus 로고    scopus 로고
    • (Gilead Sciences, Inc.). Antiviral Phosphonomethoxy Nucleotide Analogs Having Increased Oral Bioavailability.
    • US Patent 5,922,695
    • Armilli, M. N.; Kundy, K. C.; Dougherty, J. P. et al. (Gilead Sciences, Inc.). Antiviral Phosphonomethoxy Nucleotide Analogs Having Increased Oral Bioavailability. US Patent 5,922,695, 1999.
    • (1999)
    • Armilli, M.N.1    Kundy, K.C.2    Dougherty, J.P.3
  • 43
    • 84902431600 scopus 로고    scopus 로고
    • (Daiichi Seiyaku Co.). Method for Preparation of Optically Active [(nitrophenoxy)methyl]oxiranes.
    • Japan. Patent JP2000302772.
    • Takayanagi, Y.; Yokoyama, S. (Daiichi Seiyaku Co.). Method for Preparation of Optically Active [(nitrophenoxy)methyl]oxiranes. Japan. Patent JP2000302772.
    • Takayanagi, Y.1    Yokoyama, S.2
  • 44
    • 84902426537 scopus 로고    scopus 로고
    • (Rhodia ChiRex, Inc.). Process for the Preparation of (R)-1-(aryloxy)propan-2-ol.
    • US Patent 6,448,449
    • Larrow, J. F. (Rhodia ChiRex, Inc.). Process for the Preparation of (R)-1-(aryloxy)propan-2-ol. US Patent 6,448,449, 2002.
    • (2002)
    • Larrow, J.F.1
  • 48
    • 84902416123 scopus 로고    scopus 로고
    • (Rhodia Pharma Solutions) Kinetic Resolution Method
    • US Patent 6,639,087
    • Larrow, J. F.; Jasmin, S.; Liu, Y.; DiMare, M. (Rhodia Pharma Solutions) Kinetic Resolution Method. US Patent 6,639,087, 2003.
    • (2003)
    • Larrow, J.F.1    Jasmin, S.2    Liu, Y.3    DiMare, M.4
  • 49
    • 84902426459 scopus 로고    scopus 로고
    • This chiral building block has been primarily used to generate enantiopure 3-(aminomethyl)-morpholine derivatives useful as CCR-3 antagonists for the treatment of asthma. For example, see: Ancliff, R. A.; Cook, C. M.; Eldred, C. D.; et al. (Glaxo Group Ltd). Preparation of N-(morpholin-2-yl)methylacetamides as CCR-3 Antagonists Useful in the Treatment of Inflammatory Diseases. International Patent Appl. WO 2003082863 A1, 2003.
    • This chiral building block has been primarily used to generate enantiopure 3-(aminomethyl)-morpholine derivatives useful as CCR-3 antagonists for the treatment of asthma. For example, see: Ancliff, R. A.; Cook, C. M.; Eldred, C. D.; et al. (Glaxo Group Ltd). Preparation of N-(morpholin-2-yl)methylacetamides as CCR-3 Antagonists Useful in the Treatment of Inflammatory Diseases. International Patent Appl. WO 2003082863 A1, 2003.
  • 50
    • 84888613779 scopus 로고    scopus 로고
    • (Bracco International, B. V.). Heteroatom Bearing Ligands and Metal Complexes Thereof.
    • US Patent 5,608,110
    • Ramalingam, K.; Raju, N. (Bracco International, B. V.). Heteroatom Bearing Ligands and Metal Complexes Thereof. US Patent 5,608,110, 1997.
    • (1997)
    • Ramalingam, K.1    Raju, N.2
  • 54
    • 84902422980 scopus 로고    scopus 로고
    • (F. Hoffmann-La Roche AG). Process for the Preparation of (S)-4-(fluoromethyl)dihydrofuran-2-one.
    • US Patent Appl. 2008108816 A1
    • Zutter, U. (F. Hoffmann-La Roche AG). Process for the Preparation of (S)-4-(fluoromethyl)dihydrofuran-2-one. US Patent Appl. 2008108816 A1, 2008.
    • (2008)
    • Zutter, U.1
  • 55
    • 84902433792 scopus 로고    scopus 로고
    • (F. Hoffmann-La Roche AG). Preparation of (S)-4-fluoromethyl-dihydro-furan-2-one and its Use in Synthesis of Pyrido[2,1-a]isoquinoline Derivatives.
    • International Patent Appl. WO 2006125728 A1
    • Abrecht, S.; Adam, J.-M.; Fettes, A.; et al. (F. Hoffmann-La Roche AG). Preparation of (S)-4-fluoromethyl-dihydro-furan-2-one and its Use in Synthesis of Pyrido[2,1-a]isoquinoline Derivatives. International Patent Appl. WO 2006125728 A1, 2006.
    • (2006)
    • Abrecht, S.1    Adam, J.-M.2    Fettes, A.3
  • 59
    • 84902426460 scopus 로고    scopus 로고
    • BRITEST site.
    • BRITEST site. http://www.britest.co.uk.
  • 64
    • 77954769635 scopus 로고    scopus 로고
    • For a recent review of this area, see:, and references therein. Also see ref. 13b
    • Zulauf A., Mellah M., Hong X., Schulz E. Dalton Transac. 2010, 39(30):6911-6935. For a recent review of this area, see:, and references therein. Also see ref. 13b.
    • (2010) Dalton Transac. , vol.39 , Issue.30 , pp. 6911-6935
    • Zulauf, A.1    Mellah, M.2    Hong, X.3    Schulz, E.4
  • 65
    • 77950274370 scopus 로고    scopus 로고
    • For an interesting discussion of the benefits of continuous flow reactors relative to traditional batch chemistry, see:, and references therein
    • Valera F.E., Quaranta M., Moran A., et al. Angew. Chem. Int. Ed. 2010, 49(14):2478-2485. For an interesting discussion of the benefits of continuous flow reactors relative to traditional batch chemistry, see:, and references therein.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , Issue.14 , pp. 2478-2485
    • Valera, F.E.1    Quaranta, M.2    Moran, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.