메뉴 건너뛰기




Volumn 52, Issue 14, 2013, Pages 3822-3863

Industrial applications of the Diels-Alder reaction

Author keywords

cycloaddition; Diels Alder reaction; industrial chemistry; process chemistry; synthetic methods

Indexed keywords

DIELS-ALDER REACTION; INDUSTRIAL CHEMISTRY; INDUSTRIAL SYNTHESIS; LARGE-SCALE APPLICATIONS; MOLECULAR COMPLEXITY; PROCESS CHEMISTRY; RESEARCH AND DEVELOPMENT; SYNTHETIC METHODS;

EID: 84875695231     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201636     Document Type: Review
Times cited : (242)

References (410)
  • 3
    • 0036259981 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 1668-1698.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1668-1698
  • 4
    • 84875707514 scopus 로고    scopus 로고
    • A. Fredga, to be found under: http://www.nobelprize.org/nobel-prizes/ chemistry/laureates/1950/press.html.
    • Fredga, A.1
  • 12
    • 0036263839 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 1650-1667.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1650-1667
  • 16
    • 0004148431 scopus 로고    scopus 로고
    • Wiley, Hoboken
    • for reviews on intramolecular DA reactions, see, E. Ciganek, in Organic Reactions, Vol. 32, Wiley, Hoboken, 2004
    • (2004) Organic Reactions , vol.32
    • Ciganek, E.1
  • 18
    • 0000048258 scopus 로고
    • (Eds.: M. T. Barry, F. Ian), Pergamon, Oxford
    • O. Wolfgang, in Comprehensive Organic Synthesis (Eds.:, M. T. Barry, F. Ian,), Pergamon, Oxford, 1991, pp. 315-399.
    • (1991) Comprehensive Organic Synthesis , pp. 315-399
    • Wolfgang, O.1
  • 19
    • 84875744650 scopus 로고
    • For a short selection of examples of cycloadditions in industrial syntheses, see, H. Koenig, Stud. Org. Chem. 1981, 6, 201-221.
    • (1981) Stud. Org. Chem. , vol.6 , pp. 201-221
    • Koenig, H.1
  • 20
    • 33747041670 scopus 로고    scopus 로고
    • T. Y. Zhang, Chem. Rev. 2006, 106, 2583-2595.
    • (2006) Chem. Rev. , vol.106 , pp. 2583-2595
    • Zhang, T.Y.1
  • 25
    • 78249273274 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 8082-8091.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8082-8091
  • 27
    • 84875754052 scopus 로고    scopus 로고
    • J. T. Njardarson, to be found under: http://cbc.arizona.edu/njardarson/ group/sites/default/files/ Top%20200%20Generic%20Drugs%20by%20Retail%20Dollars%20in%202008%281%29.pdf.
    • Njardarson, J.T.1
  • 38
    • 79951914183 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 1974-1976
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 1974-1976
  • 45
    • 79952637489 scopus 로고    scopus 로고
    • After this survey was initiated, a review illustrating the frequent use of the Suzuki reaction on scale appeared:, J. Magano, J. R. Dunetz, Chem. Rev. 2011, 111, 2177-2250.
    • (2011) Chem. Rev. , vol.111 , pp. 2177-2250
    • Magano, J.1    Dunetz, J.R.2
  • 48
    • 84875693007 scopus 로고    scopus 로고
    • (Koninklijke Philips Electronics N.V.), WO2004083160A1
    • Applications in the field of polymer chemistry for the synthesis of organic thin film, photosensitive material, ink, resin, paper, albeit numerous, are not covered. See, for example, for organic thin film:, H. W. Ten, B.-H. Huisman, (Koninklijke Philips Electronics N.V.), WO2004083160A1, 2004; antifouling paint
    • (2004)
    • Ten, H.W.1    Huisman, B.-H.2
  • 49
    • 84875700376 scopus 로고    scopus 로고
    • (Chugoku Marine Paints, Ltd.), WO2005051884A1
    • T. Nishiguchi, N. Nakamura, M. Tsuboi, (Chugoku Marine Paints, Ltd.), WO2005051884A1, 2005; for light-emitting diodes
    • (2005)
    • Nishiguchi, T.1    Nakamura, N.2    Tsuboi, M.3
  • 50
    • 84875744107 scopus 로고    scopus 로고
    • (Ciba Specialty Chemicals Holding Inc.), WO2008012250A1
    • T. Schaefer, K. Müllen, M. G. R. Turbiez, M. Baumgarten, (Ciba Specialty Chemicals Holding Inc.), WO2008012250A1, 2008; for corrosion inhibitors
    • (2008)
    • Schaefer, T.1    Müllen, K.2    Turbiez, M.G.R.3    Baumgarten, M.4
  • 51
    • 84875712495 scopus 로고    scopus 로고
    • E. A. Bardasz, (Union Camp Corp.), US5066461A, 1991; for resins
    • E. A. Bardasz, (Union Camp Corp.), US5066461A, 1991; for resins
  • 60
    • 84875741753 scopus 로고    scopus 로고
    • (Monsanto Technology LLC.), WO2001070760A1
    • M. M. Schwartz, (Monsanto Technology LLC.), WO2001070760A1, 2001
    • (2001)
    • Schwartz, M.M.1
  • 65
    • 84875739914 scopus 로고    scopus 로고
    • D. H. R. Barton, R. H. Hesse, E. Rizzardo, (Research Institute for Medicine and Chemistry, Inc.), DE2400931A1, 1974
    • D. H. R. Barton, R. H. Hesse, E. Rizzardo, (Research Institute for Medicine and Chemistry, Inc.), DE2400931A1, 1974.
  • 77
    • 84875714977 scopus 로고
    • (Leo Pharmaceutical Products Ltd.), WO8700834A1
    • M. J. Calverley, E. T. Binderup, (Leo Pharmaceutical Products Ltd.), WO8700834A1, 1987.
    • (1987)
    • Calverley, M.J.1    Binderup, E.T.2
  • 80
    • 84875711790 scopus 로고
    • (American Home Products), US3170936
    • P. F. Morand, R. Deghenghi, (American Home Products), US3170936, 1965
    • (1965)
    • Morand, P.F.1    Deghenghi, R.2
  • 81
    • 84875745348 scopus 로고
    • (American Home Products), US5428151A
    • M. W. Winkley, R. D. Mitchell, (American Home Products), US5428151A, 1995.
    • (1995)
    • Winkley, M.W.1    Mitchell, R.D.2
  • 84
    • 33845376451 scopus 로고
    • For a review, see, D. L. Boger, Chem. Rev. 1986, 86, 781-793.
    • (1986) Chem. Rev. , vol.86 , pp. 781-793
    • Boger, D.L.1
  • 88
    • 84875758055 scopus 로고
    • (Hoffmann-La Roche), FR1384099
    • W. Kimel, W. Leimgruber, (Hoffmann-La Roche), FR1384099, 1965.
    • (1965)
    • Kimel, W.1    Leimgruber, W.2
  • 89
    • 84875726650 scopus 로고
    • (Henkel), DE2918168A1
    • For other industrial applications of dioxepin as a dienophile in the perfume industry, see, J. Conrad, H. Upadek, K. Bruns, (Henkel), DE2918168A1, 1980.
    • (1980)
    • Conrad, J.1    Upadek, H.2    Bruns, K.3
  • 92
    • 84875721447 scopus 로고
    • (BASF), DE3141443A1
    • H. Kiefer, (BASF), DE3141443A1, 1983.
    • (1983)
    • Kiefer, H.1
  • 95
    • 84875718692 scopus 로고
    • (Nippon Shokubai Kagaku Kogyo Co., Ltd.), US4840749
    • The industrial preparation of 1-aminoanthraquinone from 5-nitro-1,4-naphthoquinone following a similar approach was reported, see, N. Ikeda, N. Sugishima, Y. Fujii, S. Ikuta, Y. Nakanishi, A. Inoue, (Nippon Shokubai Kagaku Kogyo Co., Ltd.), US4840749, 1987.
    • (1987)
    • Ikeda, N.1    Sugishima, N.2    Fujii, Y.3    Ikuta, S.4    Nakanishi, Y.5    Inoue, A.6
  • 109
  • 117
    • 84875749499 scopus 로고    scopus 로고
    • Dr. I. Veselý (Cayman Pharma): personal communication
    • Dr. I. Veselý (Cayman Pharma): personal communication.
  • 124
    • 84875697939 scopus 로고
    • (Knoll), US2789110
    • W. Klavehn, (Knoll), US2789110, 1957.
    • (1957)
    • Klavehn, W.1
  • 127
    • 84875695031 scopus 로고    scopus 로고
    • (Mitsui Toatsu Chemicals, Inc., Japan), EP785186A1
    • For an illustration of this chemistry in a continuous mode at Mitsui Chemicals, see, M. Inomata, M. Takeno, A. Numa, H. Mizutani, M. Ebina, I. Fukada, (Mitsui Toatsu Chemicals, Inc., Japan), EP785186A1, 1997.
    • (1997)
    • Inomata, M.1    Takeno, M.2    Numa, A.3    Mizutani, H.4    Ebina, M.5    Fukada, I.6
  • 128
    • 84875708983 scopus 로고    scopus 로고
    • Asta-Werke, GB826830, 1960
    • Asta-Werke, GB826830, 1960.
  • 129
    • 84875723466 scopus 로고    scopus 로고
    • Eli Lilly & Co., GB915236, 1963
    • Eli Lilly & Co., GB915236, 1963
  • 135
    • 84875755818 scopus 로고    scopus 로고
    • (Sumitomo Pharmaceuticals), WO2005009999A1
    • Y. Kakiya, M. Oda, (Sumitomo Pharmaceuticals), WO2005009999A1, 2005
    • (2005)
    • Kakiya, Y.1    Oda, M.2
  • 136
  • 137
    • 44349126622 scopus 로고    scopus 로고
    • For details about the synthesis of the starting material of this sequence, see, J. B. Matson, R. H. Grubbs, J. Am. Chem. Soc. 2008, 130, 6731-6733.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 6731-6733
    • Matson, J.B.1    Grubbs, R.H.2
  • 144
    • 84875740037 scopus 로고    scopus 로고
    • (Hoffman-La Roche), US20080154043A1
    • P. Spurr, B. Wirz, (Hoffman-La Roche), US20080154043A1, 2008.
    • (2008)
    • Spurr, P.1    Wirz, B.2
  • 148
    • 70349095283 scopus 로고    scopus 로고
    • J. Magano, Chem. Rev. 2009, 109, 4398-4438, and references therein dealing with the current manufacturing route and alternatives approaches
    • (2009) Chem. Rev. , vol.109 , pp. 4398-4438
    • Magano, J.1
  • 149
  • 151
    • 84875694982 scopus 로고    scopus 로고
    • (Isis Pharmaceuticals), WO2005049621A1
    • R. Vasulinga, Z. Wang, K. K. Raju, (Isis Pharmaceuticals), WO2005049621A1, 2005.
    • (2005)
    • Vasulinga, R.1    Wang, Z.2    Raju, K.K.3
  • 153
    • 84875698871 scopus 로고    scopus 로고
    • Prof. A. Montaña (University of Barcelona): personal communication
    • Prof. A. Montaña (University of Barcelona): personal communication.
  • 159
    • 84875714011 scopus 로고    scopus 로고
    • (Merck Sharp & Dohme), WO2006018663A1
    • S. P. Keen, S. F. Oliver, G. W. Stewart, (Merck Sharp & Dohme), WO2006018663A1, 2006.
    • (2006)
    • Keen, S.P.1    Oliver, S.F.2    Stewart, G.W.3
  • 160
    • 0142196137 scopus 로고    scopus 로고
    • For a review on the Diels-Alder reaction of anthracene derivatives, see, J. C. C. Atherton, S. Jones, Tetrahedron 2003, 59, 9039-9057.
    • (2003) Tetrahedron , vol.59 , pp. 9039-9057
    • Atherton, J.C.C.1    Jones, S.2
  • 177
    • 84875751307 scopus 로고    scopus 로고
    • (Teva Pharmaceutical), WO2009155403A2
    • For an additional discussion on this process, see, V. K. Kansal, S. Ahmad, A. Gupta, (Teva Pharmaceutical), WO2009155403A2, 2009.
    • (2009)
    • Kansal, V.K.1    Ahmad, S.2    Gupta, A.3
  • 178
    • 84875748680 scopus 로고    scopus 로고
    • For a thorough investigation by the US Chemical Safety and Hazard Investigation Board of a fatal accident during the cracking and metalation of the methylcyclopentadiene dimer to produce methylcyclopentadienyl manganese tricarbonyl, see http://www.chemsafety.gov/UserFiles/file/T2%20Final%20Report. pdf.
  • 179
    • 84875720550 scopus 로고    scopus 로고
    • (Albemarle), WO2006011873A1
    • J. C. Prindle, Jr., D. J. Manuel, (Albemarle), WO2006011873A1, 2006.
    • (2006)
    • Prindle, Jr.J.C.1    Manuel, D.J.2
  • 188
    • 84885773020 scopus 로고    scopus 로고
    • (Eds.: H. U. Blaser, H. J. Federsel), Wiley-VCH, Weinheim
    • D. Spielvogel, in Asymmetric Catalysis on Industrial Scale (Eds.:, H. U. Blaser, H. J. Federsel,), Wiley-VCH, Weinheim, 2010, pp. 219-229.
    • (2010) Asymmetric Catalysis on Industrial Scale , pp. 219-229
    • Spielvogel, D.1
  • 190
    • 84875747734 scopus 로고    scopus 로고
    • D. Spielvogel (Solvias): personal communication
    • D. Spielvogel (Solvias): personal communication.
  • 196
    • 84875755373 scopus 로고    scopus 로고
    • (Kuraray), EP1048650A2
    • a similar approach has been patented:, T. Fukumoto, R. Ikarashi, (Kuraray), EP1048650A2, 2000.
    • (2000)
    • Fukumoto, T.1    Ikarashi, R.2
  • 203
    • 84875723775 scopus 로고    scopus 로고
    • (Bayer), DE10207410C1
    • M. Loegers, (Bayer), DE10207410C1, 2003.
    • (2003)
    • Loegers, M.1
  • 207
    • 79958286197 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 5630-5647.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5630-5647
  • 208
    • 84875749624 scopus 로고    scopus 로고
    • (Lonza), WO2011023374A1
    • M. Franzen, C. Noti, (Lonza), WO2011023374A1, 2011.
    • (2011)
    • Franzen, M.1    Noti, C.2
  • 209
    • 84875706193 scopus 로고    scopus 로고
    • Dr. C. Noti (Lonza): personal communication
    • Dr. C. Noti (Lonza): personal communication.
  • 215
    • 84875695120 scopus 로고    scopus 로고
    • Performed on 100 g scale: Dr. E. Lawson (Johnson and Johnson): personal communication
    • Performed on 100 g scale: Dr. E. Lawson (Johnson and Johnson): personal communication.
  • 229
    • 84875703601 scopus 로고
    • (Kuraray), EP640579A2
    • M. Toprihara, Y. Tama, (Kuraray), EP640579A2, 1995.
    • (1995)
    • Toprihara, M.1    Tama, Y.2
  • 232
    • 84875711065 scopus 로고    scopus 로고
    • Dr N. Yoshida (Chisso Corp): personal communication
    • Dr N. Yoshida (Chisso Corp): personal communication.
  • 241
    • 84875725644 scopus 로고    scopus 로고
    • M. Weber in Scale-Up of a Cathepsin K Inhibitor (MK-1256) that is Efficacious in a Potential Treatment for Osteoporosis, Organic Processs Research & Development, Lisbon, Portugal, September 9-11, 2009
    • M. Weber in Scale-Up of a Cathepsin K Inhibitor (MK-1256) that is Efficacious in a Potential Treatment for Osteoporosis, Organic Processs Research & Development, Lisbon, Portugal, September 9-11, 2009.
  • 247
    • 33746933200 scopus 로고    scopus 로고
    • for a review on the use cis-1-amino-2-indanol, see, I. Gallou, C. H. Senanayake, Chem. Rev. 2006, 106, 2843-2874.
    • (2006) Chem. Rev. , vol.106 , pp. 2843-2874
    • Gallou, I.1    Senanayake, C.H.2
  • 251
    • 84875745953 scopus 로고    scopus 로고
    • Dr. W. Greenlee (Merck): personal communication
    • Dr. W. Greenlee (Merck): personal communication.
  • 264
    • 84875747854 scopus 로고    scopus 로고
    • (Astra Zeneca), WO2009101432A2
    • M. R. Fielding, J. Leonard, (Astra Zeneca), WO2009101432A2, 2009.
    • (2009)
    • Fielding, M.R.1    Leonard, J.2
  • 272
    • 84875694531 scopus 로고    scopus 로고
    • (Mallinckrodt), US20100081816A1
    • A. Mannino, J. Zdrodowski, (Mallinckrodt), US20100081816A1, 2010.
    • (2010)
    • Mannino, A.1    Zdrodowski, J.2
  • 277
    • 0001758707 scopus 로고
    • For a general discussion on the reactivity of this diene and its synthesis, see, M. E. Jung, C. A. Mc Combs, Org. Synth. 1978, 58, 163
    • (1978) Org. Synth. , vol.58 , pp. 163
    • Jung, M.E.1    Mc Combs, C.A.2
  • 284
    • 84875723688 scopus 로고    scopus 로고
    • (Actelion Pharmaceuticals Ltd.), WO2008132679A1
    • K. Hilpert, F. Hubler, D. Renneberg, (Actelion Pharmaceuticals Ltd.), WO2008132679A1, 2008.
    • (2008)
    • Hilpert, K.1    Hubler, F.2    Renneberg, D.3
  • 288
    • 84875697207 scopus 로고
    • (Farberke Hoechst), DE1015797
    • H. Frensch, H. Goebel, (Farberke Hoechst), DE1015797, 1957
    • (1957)
    • Frensch, H.1    Goebel, H.2
  • 290
    • 84875742066 scopus 로고    scopus 로고
    • To be found under: http://www.inchem.org/documents/ehc/ehc/ehc40.htm.
  • 291
    • 84875750909 scopus 로고
    • (Van Dyk & Co.), US2476512
    • A. A. Schreiber, (Van Dyk & Co.), US2476512, 1949.
    • (1949)
    • Schreiber, A.A.1
  • 294
    • 84875721933 scopus 로고
    • (BASF), DE1935009A
    • F. Graf, H. Koenig, (BASF), DE1935009A, 1971.
    • (1971)
    • Graf, F.1    Koenig, H.2
  • 299
    • 84875732893 scopus 로고
    • (Shell), BE616856
    • E. E. Young, (Shell), BE616856, 1962.
    • (1962)
    • Young, E.E.1
  • 306
    • 84875758830 scopus 로고    scopus 로고
    • (Syngenta), WO2008017443A1
    • H. Walter, U. Nettekoven, (Syngenta), WO2008017443A1, 2008.
    • (2008)
    • Walter, H.1    Nettekoven, U.2
  • 308
    • 52049105452 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6338-6361.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6338-6361
  • 321
    • 84875755949 scopus 로고    scopus 로고
    • To be found under: http://www.fda.gov/Drugs/ GuidanceComplianceRegulatoryInformation/Guidances/ucm122883.htm.
  • 322
    • 84875710811 scopus 로고    scopus 로고
    • To be found under: http://ec.europa.eu/health/files/eudralex/vol-7/b/ 7bq4a-en.pdf.
  • 326
    • 0000883249 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 2980-3010.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2980-3010
  • 327
    • 0004119218 scopus 로고    scopus 로고
    • (Ed.: C. S. Sell), The Royal Society of Chemistry, London
    • C. Sell, in Chemistry of Fragrances (Ed.:, C. S. Sell,), The Royal Society of Chemistry, London, 1999. pp. 52-131.
    • (1999) Chemistry of Fragrances , pp. 52-131
    • Sell, C.1
  • 328
    • 84875735307 scopus 로고    scopus 로고
    • Food Chem. Toxicol. 2000, 38, Supplement 3, s137-s141.
    • (2000) Food Chem. Toxicol. , vol.38 , Issue.SUPPLEMENT 3
  • 329
    • 84875722491 scopus 로고
    • (N.V. Chemische Fabriek "Naarden"), NL6901750A
    • B. D. Frank, (N.V. Chemische Fabriek "Naarden"), NL6901750A, 1970
    • (1970)
    • Frank, B.D.1
  • 330
    • 84875692372 scopus 로고
    • (International Flavors and Fragrances), US4275251A
    • M. A. Sprecker, J. B. Hall, (International Flavors and Fragrances), US4275251A, 1981
    • (1981)
    • Sprecker, M.A.1    Hall, J.B.2
  • 334
    • 84875721644 scopus 로고
    • (BASF), DE2719976A1
    • W. Hoffmann, F. K. Von, (BASF), DE2719976A1, 1978.
    • (1978)
    • Hoffmann, W.1    Von, F.K.2
  • 340
    • 70349915725 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 7221-7223.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7221-7223
  • 342
    • 53249140774 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6634-6637.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6634-6637
  • 343
    • 84875693575 scopus 로고    scopus 로고
    • (International Flavors and Fragrances), US20100092418A1
    • A. P. Closson, A. T. Levorse, Jr., M. G. Monteleone, (International Flavors and Fragrances), US20100092418A1, 2010
    • (2010)
    • Closson, A.P.1    Levorse, Jr.A.T.2    Monteleone, M.G.3
  • 345
    • 84875697683 scopus 로고    scopus 로고
    • (Givaudan), WO2009021342A2
    • A. Goeke, Y. Zou, (Givaudan), WO2009021342A2, 2009
    • (2009)
    • Goeke, A.1    Zou, Y.2
  • 347
    • 84875736309 scopus 로고
    • (N.V. Chemische Fabriek "Naarden"), DE2221949A
    • D. de Rijke, H. Boelens, (N.V. Chemische Fabriek "Naarden"), DE2221949A, 1972
    • (1972)
    • De Rijke, D.1    Boelens, H.2
  • 349
    • 84875759106 scopus 로고
    • (Takasago Perfumery Co., Ltd.), DE2833283A1
    • T. Kobayashi, H. Tsuruta, T. Yoshida, (Takasago Perfumery Co., Ltd.), DE2833283A1, 1979.
    • (1979)
    • Kobayashi, T.1    Tsuruta, H.2    Yoshida, T.3
  • 352
    • 84875746796 scopus 로고    scopus 로고
    • Naarden International, NL8601541A, 1988
    • Naarden International, NL8601541A, 1988.
  • 353
    • 84875719784 scopus 로고
    • (Dragoco), DE3317476A1
    • E. J. Brunke, H. Struwe, (Dragoco), DE3317476A1, 1984.
    • (1984)
    • Brunke, E.J.1    Struwe, H.2
  • 354
    • 84875733048 scopus 로고    scopus 로고
    • (Givaudan), EP1318190A1
    • A. Goeke, (Givaudan), EP1318190A1, 2003.
    • (2003)
    • Goeke, A.1
  • 355
    • 84875694283 scopus 로고    scopus 로고
    • (Quest International), WO2004048336A1
    • D. Munro, (Quest International), WO2004048336A1, 2004.
    • (2004)
    • Munro, D.1
  • 358
    • 84875757090 scopus 로고
    • (Hercules Powder), US2406106
    • A. L. Rummelsburg, (Hercules Powder), US2406106, 1946.
    • (1946)
    • Rummelsburg, A.L.1
  • 359
    • 84875725374 scopus 로고
    • (International Flavors and Fragrances), US2947780
    • R. W. Teegarden, L. Steinbach, (International Flavors and Fragrances), US2947780, 1960.
    • (1960)
    • Teegarden, R.W.1    Steinbach, L.2
  • 360
    • 84875709348 scopus 로고
    • (International Flavors and Fragrances), US4007137A
    • J. M. Sanders, W. L. Schreiber, J. B. Hall, (International Flavors and Fragrances), US4007137A, 1977.
    • (1977)
    • Sanders, J.M.1    Schreiber, W.L.2    Hall, J.B.3
  • 363
    • 84875725600 scopus 로고
    • (Givaudan), US2842598
    • G. C. Kitchens, (Givaudan), US2842598, 1958
    • (1958)
    • Kitchens, G.C.1
  • 364
  • 365
    • 84875696302 scopus 로고
    • (Dragoco), DE1057108
    • G. Ohloff, (Dragoco), DE1057108, 1959.
    • (1959)
    • Ohloff, G.1
  • 366
    • 84875720462 scopus 로고
    • (Dragoco), GB896039
    • G. Ohloff, (Dragoco), GB896039, 1962.
    • (1962)
    • Ohloff, G.1
  • 367
    • 84875743792 scopus 로고
    • (International Flavors and Fragrances), US3929677A
    • J. B. Hall, J. M. Sanders, (International Flavors and Fragrances), US3929677A, 1975.
    • (1975)
    • Hall, J.B.1    Sanders, J.M.2
  • 371
    • 84875696210 scopus 로고    scopus 로고
    • (Givaudan), WO2006086908A1
    • F. Schroeder, (Givaudan), WO2006086908A1, 2006
    • (2006)
    • Schroeder, F.1
  • 383
    • 84875745905 scopus 로고
    • (Firmenich S. A., Switz.), CH655932A5
    • C. Tarchini, (Firmenich S. A., Switz.), CH655932A5, 1986
    • (1986)
    • Tarchini, C.1
  • 384
    • 84875724708 scopus 로고
    • (Henkel), US4348543A
    • E. R. Rogier, (Henkel), US4348543A, 1982.
    • (1982)
    • Rogier, E.R.1
  • 385
  • 386
    • 84875726366 scopus 로고
    • (Henkel), EP53717A1
    • H. Upadek, K. Bruns, (Henkel), EP53717A1, 1982
    • (1982)
    • Upadek, H.1    Bruns, K.2
  • 388
    • 84875734879 scopus 로고
    • (Union Camp Corp.), US5066461A
    • terpinene-derived starting materials have been used as well in the polymer industry for the preparation of corrosion inhibitors; a 5 kg protocol was reported: E. A. Bardasz, (Union Camp Corp.), US5066461A, 1991.
    • (1991)
    • Bardasz, E.A.1
  • 393
  • 399
    • 84875702621 scopus 로고
    • (International Flavors and Fragrances), US4560500A
    • W. J. Wiegers, (International Flavors and Fragrances), US4560500A, 1985.
    • (1985)
    • Wiegers, W.J.1
  • 402
    • 33747054198 scopus 로고    scopus 로고
    • In 2006, Farina et al. had already alluded to this point with the following comment: "although the [enantioselective DA reaction] is relatively well developed, applications to API synthesis have not been forthcoming":, V. Farina, J. T. Reeves, C. H. Senanayake, J. J. Song, Chem. Rev. 2006, 106, 2734-2793.
    • (2006) Chem. Rev. , vol.106 , pp. 2734-2793
    • Farina, V.1    Reeves, J.T.2    Senanayake, C.H.3    Song, J.J.4
  • 404
    • 84875737517 scopus 로고    scopus 로고
    • 13 May
    • The Wall Street Journal, 13 May 2011, Researchers Manipulate Drug's Chemistry in Bid to Lower Treatment Cost, to be found under
    • (2011) The Wall Street Journal
  • 405
    • 84875717705 scopus 로고    scopus 로고
    • http://online.wsj.com/article/ SB10001424052748703730804576319480990825422.html?mod=WSJ-business-IndustryNews- DHC.
  • 407
    • 84871953839 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 12960-12990.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 12960-12990
  • 410
    • 84984215074 scopus 로고
    • (see Scheme S20 in the Supporting Information)
    • J. Leitich, G. Sprintschnik, Chem. Ber. 1986, 119, 1640-1660 (see Scheme S20 in the Supporting Information).
    • (1986) Chem. Ber. , vol.119 , pp. 1640-1660
    • Leitich, J.1    Sprintschnik, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.