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Volumn , Issue 15, 2003, Pages 2354-2358

Pd-Catalysed Synthesis of 5-Substituted Proline Derivatives from Acetylene-Containing Amino Acids

Author keywords

Acetylenes; Amino acids; Cyclisations; Pd catalysis; Proline derivatives

Indexed keywords

ACETONITRILE; ACETYLENE DERIVATIVE; AMINO ACID; PALLADIUM; PROLINE DERIVATIVE; PYRROLINE DERIVATIVE; SILANE DERIVATIVE; TRIFLUOROACETIC ACID;

EID: 0347380044     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43337     Document Type: Article
Times cited : (14)

References (33)
  • 20
    • 0001188647 scopus 로고    scopus 로고
    • This trifunctional amino acid(propargylglycine) is commercially available, but in our group also readily prepared via a chemo-enzymatic procedure that has been developed in collaboration with DSM Research (Geleen, The Netherlands): (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000, 23.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 662
    • Wolf, L.B.1    Sonke, T.2    Tjen, K.C.M.F.3    Kaptein, B.4    Broxterman, Q.B.5    Schoemaker, H.E.6    Rutjes, F.P.J.T.7
  • 21
    • 0002267204 scopus 로고    scopus 로고
    • Patel, R. N., Ed.; Marcel Dekker: New York
    • This trifunctional amino acid(propargylglycine) is commercially available, but in our group also readily prepared via a chemo-enzymatic procedure that has been developed in collaboration with DSM Research (Geleen, The Netherlands): (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000, 23.
    • (2000) Stereoselective Biocatalysis , pp. 23
    • Sonke, T.1    Kaptein, B.2    Boesten, W.H.J.3    Broxterman, Q.B.4    Kamphuis, J.5    Formaggio, F.6    Toniolo, C.7    Rutjes, F.P.J.T.8    Schoemaker, H.E.9
  • 25
    • 0347812008 scopus 로고    scopus 로고
    • note
    • 13C NMR, high resolution mass data and rotational values.
  • 26
    • 0037124432 scopus 로고    scopus 로고
    • Similar elimination of p-toluenesulfinic acid from sulfonamide moieties has previously been observed: (a) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491. (b) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S.; Sacramento, J. J. Chem. Soc., Perkin Trans. 1 2001, 3167.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4491
    • Ferreira, P.M.T.1    Maia, H.L.S.2    Monteiro, L.S.3
  • 29
    • 0347812007 scopus 로고    scopus 로고
    • note
    • Crystallographic data of structures 21 and 26 have both been deposited at the Cambridge Crystallographic Data Centre and have been allocated the deposition numbers CCDC 212273 and CCDC 212274, respectively.
  • 30
    • 0345920782 scopus 로고    scopus 로고
    • note
    • To determine the enantiopurity of compound 24, racemic 24 was synthesised and separated on a Chiralcel OD column (eluant: i-PrOH/hexane = 1:9). Using this assay, the ee of pyrroline 24 was determined to be >99%.
  • 32
    • 0034625424 scopus 로고    scopus 로고
    • For a review on N-acyliminium ions and related structures, see: Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
    • (2000) Tetrahedron , vol.56 , pp. 3817
    • Speckamp, W.N.1    Moolenaar, M.J.2
  • 33
    • 0347812006 scopus 로고    scopus 로고
    • note
    • 4S: 359.1191. Found: 359.1183.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.