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Volumn 65, Issue 6, 2000, Pages 1750-1757

Combinatorial chemistry for ligand development in catalysis: Synthesis and catalysis screening of peptidosulfonamide tweezers on the solid phase

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DIETHYLZINC; LIGAND; PYRROLIDINE DERIVATIVE; SULFONAMIDE;

EID: 0034708568     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991628z     Document Type: Article
Times cited : (75)

References (25)
  • 2
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    • and references therein
    • (b) For a nice overview of seminal work of several researchers, see, e.g.: Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885 and references therein.
    • (1998) Chem. Eur. J. , vol.4 , pp. 1885
    • Shimizu, K.D.1    Snapper, M.L.2    Hoveyda, A.H.3
  • 9
    • 0024826461 scopus 로고
    • See e.g. Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095; Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. A modified bissulfonamide ligand derived from 2 has been used as a cross-linker in the successfull preparation of a polymeric catalytically active ligand for the enantioselective alkylation of benzaldehyde: Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510-512.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7095
    • Takahashi, H.1    Kawakita, T.2    Yoshioka, M.3    Kobayashi, S.4    Ohno, M.5
  • 10
    • 0026650218 scopus 로고
    • See e.g. Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095; Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. A modified bissulfonamide ligand derived from 2 has been used as a cross-linker in the successfull preparation of a polymeric catalytically active ligand for the enantioselective alkylation of benzaldehyde: Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510-512.
    • (1992) Tetrahedron , vol.48 , pp. 5691
    • Takahashi, H.1    Kawakita, T.2    Ohno, M.3    Yoshioka, M.4    Kobayashi, S.5
  • 11
    • 0032473520 scopus 로고    scopus 로고
    • See e.g. Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095; Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. A modified bissulfonamide ligand derived from 2 has been used as a cross-linker in the successfull preparation of a polymeric catalytically active ligand for the enantioselective alkylation of benzaldehyde: Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510-512.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 510-512
    • Halm, C.1    Kurth, M.J.2
  • 13
    • 0028906541 scopus 로고
    • This hinge was successfully applied in the synthetic receptors of Still et al.; see, e.g.: (a) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567-578. (b) Shao, Y.; Still, W. C. J. Org. Chem. 1996, 62, 6086- 6087. (c) Pan, Z.; Still, W. C.Tetrahedron Lett. 1996, 37, 8699-8702. (d) Torneiro, M.; Still, W. C.Tetrahedron 1997, 53, 8739-8750.
    • (1995) Tetrahedron , vol.51 , pp. 567-578
    • Yoon, S.S.1    Still, W.C.2
  • 14
    • 0029791484 scopus 로고    scopus 로고
    • This hinge was successfully applied in the synthetic receptors of Still et al.; see, e.g.: (a) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567-578. (b) Shao, Y.; Still, W. C. J. Org. Chem. 1996, 62, 6086-6087. (c) Pan, Z.; Still, W. C.Tetrahedron Lett. 1996, 37, 8699-8702. (d) Torneiro, M.; Still, W. C.Tetrahedron 1997, 53, 8739-8750.
    • (1996) J. Org. Chem. , vol.62 , pp. 6086-6087
    • Shao, Y.1    Still, W.C.2
  • 15
    • 0030602167 scopus 로고    scopus 로고
    • This hinge was successfully applied in the synthetic receptors of Still et al.; see, e.g.: (a) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567-578. (b) Shao, Y.; Still, W. C. J. Org. Chem. 1996, 62, 6086- 6087. (c) Pan, Z.; Still, W. C.Tetrahedron Lett. 1996, 37, 8699-8702. (d) Torneiro, M.; Still, W. C.Tetrahedron 1997, 53, 8739-8750.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8699-8702
    • Pan, Z.1    Still, W.C.2
  • 16
    • 0030854052 scopus 로고    scopus 로고
    • This hinge was successfully applied in the synthetic receptors of Still et al.; see, e.g.: (a) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567-578. (b) Shao, Y.; Still, W. C. J. Org. Chem. 1996, 62, 6086- 6087. (c) Pan, Z.; Still, W. C.Tetrahedron Lett. 1996, 37, 8699-8702. (d) Torneiro, M.; Still, W. C.Tetrahedron 1997, 53, 8739-8750.
    • (1997) Tetrahedron , vol.53 , pp. 8739-8750
    • Torneiro, M.1    Still, W.C.2
  • 19
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    • See ref 5a
    • See ref 5a.
  • 22
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    • note
    • We have now shown that although upon storage the Fmoc group is less stable, it gave rise to comparable conversions and ee.


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