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Volumn 121, Issue 27, 1999, Pages 6421-6429

Iridium-catalyzed enantioselective hydrogenation of imines in supercritical carbon dioxide

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; ANION; CARBAMIC ACID DERIVATIVE; CARBON DIOXIDE; DICHLOROMETHANE; IMINE; IRIDIUM; N (1 PHENYLETHYLIDENE)ANILINE; OXAZOLE DERIVATIVE; PHOSPHINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 0033553989     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984309i     Document Type: Article
Times cited : (301)

References (85)
  • 1
    • 0003816233 scopus 로고    scopus 로고
    • Jessop, P. G., Leitner, W., Eds.; Wiley-VCH: New York
    • Chemical Synthesis in Supercritical Fluids; Jessop, P. G., Leitner, W., Eds.; Wiley-VCH: New York, 1999.
    • (1999) Chemical Synthesis in Supercritical Fluids
  • 2
    • 0040412195 scopus 로고
    • Selected recent reviews: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065. (b) Morgenstern, D. A.; LeLacheur, R. M.; Morita, D. K.; Borkowsky, S. L.; Feng, S.; Brown, G. H.; Luan, L.; Gross, M. F.; Burk, M. J.; Tumas, W. In Green Chemistry; Anastas, P. T., Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; pp 132. (c) Dinjus, E.; Fornika, R.; Scholz, M. In Chemistry under Extreme or Non-Classical Conditions; van Eldik, R., Hubbard, C. D., Eds.; Wiley: New York, 1996; pp 219. (d) Jessop, P. G. In Fine Chemicals Catalysis II; Blackmond, D., Leitner, W., Eds.; Top. Catal. 1998, 5, 95.
    • (1995) Science , vol.269 , pp. 1065
    • Jessop, P.G.1    Ikariya, T.2    Noyori, R.3
  • 3
    • 0001646886 scopus 로고    scopus 로고
    • Anastas, P. T., Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC
    • Selected recent reviews: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065. (b) Morgenstern, D. A.; LeLacheur, R. M.; Morita, D. K.; Borkowsky, S. L.; Feng, S.; Brown, G. H.; Luan, L.; Gross, M. F.; Burk, M. J.; Tumas, W. In Green Chemistry; Anastas, P. T., Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; pp 132. (c) Dinjus, E.; Fornika, R.; Scholz, M. In Chemistry under Extreme or Non-Classical Conditions; van Eldik, R., Hubbard, C. D., Eds.; Wiley: New York, 1996; pp 219. (d) Jessop, P. G. In Fine Chemicals Catalysis II; Blackmond, D., Leitner, W., Eds.; Top. Catal. 1998, 5, 95.
    • (1996) Green Chemistry , pp. 132
    • Morgenstern, D.A.1    LeLacheur, R.M.2    Morita, D.K.3    Borkowsky, S.L.4    Feng, S.5    Brown, G.H.6    Luan, L.7    Gross, M.F.8    Burk, M.J.9    Tumas, W.10
  • 4
    • 0002544457 scopus 로고    scopus 로고
    • van Eldik, R., Hubbard, C. D., Eds.; Wiley: New York
    • Selected recent reviews: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065. (b) Morgenstern, D. A.; LeLacheur, R. M.; Morita, D. K.; Borkowsky, S. L.; Feng, S.; Brown, G. H.; Luan, L.; Gross, M. F.; Burk, M. J.; Tumas, W. In Green Chemistry; Anastas, P. T., Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; pp 132. (c) Dinjus, E.; Fornika, R.; Scholz, M. In Chemistry under Extreme or Non-Classical Conditions; van Eldik, R., Hubbard, C. D., Eds.; Wiley: New York, 1996; pp 219. (d) Jessop, P. G. In Fine Chemicals Catalysis II; Blackmond, D., Leitner, W., Eds.; Top. Catal. 1998, 5, 95.
    • (1996) Chemistry under Extreme or Non-Classical Conditions , pp. 219
    • Dinjus, E.1    Fornika, R.2    Scholz, M.3
  • 5
    • 0345309347 scopus 로고    scopus 로고
    • Blackmond, D., Leitner, W., Eds.
    • Selected recent reviews: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065. (b) Morgenstern, D. A.; LeLacheur, R. M.; Morita, D. K.; Borkowsky, S. L.; Feng, S.; Brown, G. H.; Luan, L.; Gross, M. F.; Burk, M. J.; Tumas, W. In Green Chemistry; Anastas, P. T., Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; pp 132. (c) Dinjus, E.; Fornika, R.; Scholz, M. In Chemistry under Extreme or Non-Classical Conditions; van Eldik, R., Hubbard, C. D., Eds.; Wiley: New York, 1996; pp 219. (d) Jessop, P. G. In Fine Chemicals Catalysis II; Blackmond, D., Leitner, W., Eds.; Top. Catal. 1998, 5, 95.
    • Fine Chemicals Catalysis II
    • Jessop, P.G.1
  • 6
    • 0344878198 scopus 로고    scopus 로고
    • Selected recent reviews: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065. (b) Morgenstern, D. A.; LeLacheur, R. M.; Morita, D. K.; Borkowsky, S. L.; Feng, S.; Brown, G. H.; Luan, L.; Gross, M. F.; Burk, M. J.; Tumas, W. In Green Chemistry; Anastas, P. T., Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; pp 132. (c) Dinjus, E.; Fornika, R.; Scholz, M. In Chemistry under Extreme or Non-Classical Conditions; van Eldik, R., Hubbard, C. D., Eds.; Wiley: New York, 1996; pp 219. (d) Jessop, P. G. In Fine Chemicals Catalysis II; Blackmond, D., Leitner, W., Eds.; Top. Catal. 1998, 5, 95.
    • (1998) Top. Catal. , vol.5 , pp. 95
  • 10
    • 0031471863 scopus 로고    scopus 로고
    • Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2466
  • 11
    • 0000943204 scopus 로고
    • (a) Zosel, K.; Angew. Chem. 1978, 90, 748; Angew. Chem., Int. Ed. Engl. 1978, 17, 702.
    • (1978) Angew. Chem. , vol.90 , pp. 748
    • Zosel, K.1
  • 12
    • 0018020670 scopus 로고
    • (a) Zosel, K.; Angew. Chem. 1978, 90, 748; Angew. Chem., Int. Ed. Engl. 1978, 17, 702.
    • (1978) Angew. Chem., Int. Ed. Engl. , vol.17 , pp. 702
  • 15
    • 0001458108 scopus 로고
    • For general reviews on this area see: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1995, 95, 259. (b) Leitner, W. Angew. Chem. 1995, 107, 2391; Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
    • (1995) Chem. Rev. , vol.95 , pp. 259
    • Jessop, P.G.1    Ikariya, T.2    Noyori, R.3
  • 16
    • 0001458108 scopus 로고
    • For general reviews on this area see: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1995, 95, 259. (b) Leitner, W. Angew. Chem. 1995, 107, 2391; Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
    • (1995) Angew. Chem. , vol.107 , pp. 2391
    • Leitner, W.1
  • 17
    • 33748238581 scopus 로고
    • For general reviews on this area see: (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1995, 95, 259. (b) Leitner, W. Angew. Chem. 1995, 107, 2391; Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2207
  • 25
    • 0030868052 scopus 로고    scopus 로고
    • Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem. 1997, 109, 1699; Angew. Chem., Int. Ed. Engl 1997, 36, 1628.
    • (1997) Angew. Chem., Int. Ed. Engl , vol.36 , pp. 1628
  • 26
    • 20444493628 scopus 로고    scopus 로고
    • For recent applications of this concept in catalysis see: (a) Garrol, M. A.; Holmes, A. B. Chem. Commun. 1998, 1395. (b) Monta, D. K,; Pesiri, D. R.; Scott, A. D.; Glaze, W. H.; Tumas, W. Chem. Commun. 1998, 1397. (c) Palo, D. R.; Erkey, C. Ind. Eng. Chem. Res. 1998, 37, 4203. (d) Reference 6.
    • (1998) Chem. Commun. , pp. 1395
    • Garrol, M.A.1    Holmes, A.B.2
  • 27
    • 0342975973 scopus 로고    scopus 로고
    • For recent applications of this concept in catalysis see: (a) Garrol, M. A.; Holmes, A. B. Chem. Commun. 1998, 1395. (b) Monta, D. K,; Pesiri, D. R.; Scott, A. D.; Glaze, W. H.; Tumas, W. Chem. Commun. 1998, 1397. (c) Palo, D. R.; Erkey, C. Ind. Eng. Chem. Res. 1998, 37, 4203. (d) Reference 6.
    • (1998) Chem. Commun. , pp. 1397
    • Monta, D.K.1    Pesiri, D.R.2    Scott, A.D.3    Glaze, W.H.4    Tumas, W.5
  • 28
    • 0032182252 scopus 로고    scopus 로고
    • For recent applications of this concept in catalysis see: (a) Garrol, M. A.; Holmes, A. B. Chem. Commun. 1998, 1395. (b) Monta, D. K,; Pesiri, D. R.; Scott, A. D.; Glaze, W. H.; Tumas, W. Chem. Commun. 1998, 1397. (c) Palo, D. R.; Erkey, C. Ind. Eng. Chem. Res. 1998, 37, 4203. (d) Reference 6.
    • (1998) Ind. Eng. Chem. Res. , vol.37 , pp. 4203
    • Palo, D.R.1    Erkey, C.2
  • 29
    • 0344015082 scopus 로고    scopus 로고
    • Reference 6
    • For recent applications of this concept in catalysis see: (a) Garrol, M. A.; Holmes, A. B. Chem. Commun. 1998, 1395. (b) Monta, D. K,; Pesiri, D. R.; Scott, A. D.; Glaze, W. H.; Tumas, W. Chem. Commun. 1998, 1397. (c) Palo, D. R.; Erkey, C. Ind. Eng. Chem. Res. 1998, 37, 4203. (d) Reference 6.
  • 39
    • 0026574913 scopus 로고
    • For hydrogenation of benzylimines of aryl methyl ketones in a two-phase system, see: (f) Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sinou, D. J. Chem. Soc., Chem. Commun. 1991, 1684. (g) Lensink, C.; deVries, J. G. Tetrahedron: Asymmetry 1992, 3, 235.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 235
    • Lensink, C.1    DeVries, J.G.2
  • 41
    • 0345309341 scopus 로고    scopus 로고
    • EP Patent 0256982, 1988
    • (b) Spindler, F.; Pugin, B. (Ciba-Geigy AG). EP Patent 0256982, 1988.
    • Spindler, F.1    Pugin, B.2
  • 51
    • 0000811037 scopus 로고
    • (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1992, 114, 7562. Willoughby, C. A.; Buchwald, S. L. J. Org. Chem. 1993, 58, 7629.
    • (1993) J. Org. Chem. , vol.58 , pp. 7629
    • Willoughby, C.A.1    Buchwald, S.L.2
  • 57
    • 0345309335 scopus 로고    scopus 로고
    • (a) Blaser, H.-U.; Spindler, F. In Fine Chemicals Catalysis I; Blackmond, D., Leitner, W., Eds.; Top. Catal. 1997, 4,275.
    • (1997) Top. Catal. , vol.4 , pp. 275
  • 58
    • 0001426637 scopus 로고    scopus 로고
    • (b) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
    • (1996) Angew. Chem. , vol.108 , pp. 1581
    • Togni, A.1
  • 59
    • 0029782396 scopus 로고    scopus 로고
    • (b) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1475
  • 62
    • 0000146695 scopus 로고
    • (a) von Matt, P.; Pfaltz, A. Angew. Chem. 1993, 105, 614; Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
    • (1993) Angew. Chem. , vol.105 , pp. 614
    • Von Matt, P.1    Pfaltz, A.2
  • 63
    • 33748227479 scopus 로고
    • (a) von Matt, P.; Pfaltz, A. Angew. Chem. 1993, 105, 614; Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 566
  • 66
    • 0344878186 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Basel
    • (b) Schnider, P. Ph.D. Thesis, University of Basel, 1996.
    • (1996)
    • Schnider, P.1
  • 71
    • 0002831986 scopus 로고    scopus 로고
    • Werner, H., Schreier, W., Eds.; Vieweg: Wiesbaden
    • 2-symmetric phosphinite with perfluoralkyl substituents has been previously synthesized from 2b: Kainz, S.; Koch, D.; Leitner, W. In Selective Reactions of Metal-Activated Molecules; Werner, H., Schreier, W., Eds.; Vieweg: Wiesbaden, 1998; p 151.
    • (1998) Selective Reactions of Metal-Activated Molecules , pp. 151
    • Kainz, S.1    Koch, D.2    Leitner, W.3
  • 72
    • 0000681585 scopus 로고    scopus 로고
    • The BARF anion was found to yield particularly active and selective catalysts in the enantioselective hydrogenation of nonfunctionalized C=C double bonds using the similar complexes in organic solvents: Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. Engl. 1998, 37, 2897.
    • (1998) Angew. Chem. , vol.110 , pp. 3047
    • Lightfoot, A.1    Schnider, P.2    Pfaltz, A.3
  • 73
    • 0032476793 scopus 로고    scopus 로고
    • The BARF anion was found to yield particularly active and selective catalysts in the enantioselective hydrogenation of nonfunctionalized C=C double bonds using the similar complexes in organic solvents: Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. Engl. 1998, 37, 2897.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2897
  • 74
    • 0344878182 scopus 로고    scopus 로고
    • note
    • The observations made by visual control and the pronounced influence of the composition of the mixture make other possible explanations for the activity in the second run such as accidental mechanical extrusion extremely unlikely.
  • 75
    • 0345309328 scopus 로고    scopus 로고
    • note
    • 2. Blackmond, D.; Pfaltz, A. Unpublished results.
  • 78
    • 0344446365 scopus 로고    scopus 로고
    • note
    • (c) The tube used here was manufactured in the laboratories of C. J. Elsevier, J. van't Hoff Research Institute, University of Amsterdam.
  • 81
    • 0030554252 scopus 로고    scopus 로고
    • 2 and its relevance for catalysis, see: Leitner, W. Coord. Chem. Rev. 1996, 153, 257.
    • (1996) Coord. Chem. Rev. , vol.153 , pp. 257
    • Leitner, W.1


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