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Volumn 63, Issue 48, 2007, Pages 11920-11927

Screening of chiral phosphines as catalysts for the enantioselective [3+2] annulations of N-tosylimines with allenic esters

Author keywords

3+2 Cyclisations; Asymmetric organocatalysis; Chiral phosphines; Nitrogen heterocycles; Phosphepines

Indexed keywords

CARBON; ESTER DERIVATIVE; IMINE; PHOSPHINE DERIVATIVE; PYRROLINE DERIVATIVE;

EID: 35348877267     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.022     Document Type: Article
Times cited : (100)

References (49)
  • 8
    • 35348899833 scopus 로고    scopus 로고
    • Wager, T. T.; Welch, W.; O'Neill, B. T. WO Patent 2004/110996, Pfizer, 2004;
  • 9
    • 35348836315 scopus 로고    scopus 로고
    • Segelstein, B. E.; Wager, T. T. U.S. Patent 2005/0,272,800, Pfizer, 2005;
  • 10
    • 35348857811 scopus 로고    scopus 로고
    • Humphrey, J. M.; Chappie, T. A. WO Patent 2005/115976, Pfizer, 2005.
  • 12
    • 35348859895 scopus 로고    scopus 로고
    • ®KtB.
  • 16
    • 35348922599 scopus 로고    scopus 로고
    • For representative reports see:
  • 25
    • 35348856616 scopus 로고    scopus 로고
    • See Ref. 5.
  • 29
    • 35348873461 scopus 로고    scopus 로고
    • note
    • Other well known chiral phosphines including MonoPhos, MandyPhos, Josiphos and PHOX have been evaluated. All afforded very low conversion rates and enantioselectivities.
  • 30
    • 35348868939 scopus 로고    scopus 로고
    • note
    • 37FeP: 436.1982, found: 436.2025.
  • 33
    • 33746661052 scopus 로고    scopus 로고
    • For other catalytic applications of the same phosphine, see:
    • Scherer A., and Gladysz J.A. Tetrahedron Lett. 47 (2006) 6335-6337 For other catalytic applications of the same phosphine, see:
    • (2006) Tetrahedron Lett. , vol.47 , pp. 6335-6337
    • Scherer, A.1    Gladysz, J.A.2
  • 35
    • 35348904165 scopus 로고    scopus 로고
    • note
    • Aliphatic imines have not been considered in this first screening. Compared to arylimines, they are known to give sluggish reactions with allenic esters or 2-butynoates: see Ref. 1.
  • 36
    • 35348923968 scopus 로고    scopus 로고
    • note
    • Characterisations for the new pyrroline derivatives of this series are reported in Section 3.
  • 37
    • 35348821552 scopus 로고    scopus 로고
    • For analogous reactions see:
  • 40
    • 35348916909 scopus 로고    scopus 로고
    • note
    • Further details and additional experiments will be reported later.
  • 41
    • 35348887493 scopus 로고    scopus 로고
    • note
    • Crystallographic data for compound 7a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC6. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 46
    • 35348820272 scopus 로고    scopus 로고
    • 3N/DMAP.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.