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Volumn , Issue 21, 2003, Pages 2644-2651

The complexity of catalysis: Origins of enantio- and diastereocontrol in sulfur ylide mediated epoxidation reactions

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BETAINE; BETAINE DERIVATIVE; EPOXIDE; KETONE DERIVATIVE; METAL DERIVATIVE; SOLVENT; SULFIDE; SULFUR DERIVATIVE; SULFUR YLIDE; UNCLASSIFIED DRUG;

EID: 0242525164     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b304625g     Document Type: Review
Times cited : (145)

References (50)
  • 3
    • 0000345527 scopus 로고    scopus 로고
    • eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg
    • T. Katsuki, in Comprehensive Asymmetric Catalysis II. eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg, 1999, 621.
    • (1999) Comprehensive Asymmetric Catalysis II , pp. 621
    • Katsuki, T.1
  • 4
    • 0242671578 scopus 로고    scopus 로고
    • E. N. Jacobsen and M. H. Wu, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg, 1999, 649
    • E. N. Jacobsen and M. H. Wu, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg, 1999, 649.
  • 9
    • 0001650799 scopus 로고    scopus 로고
    • eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg
    • V. K. Aggarwal, in Comprehensive Asymmetric Catalysis II, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg, 1999, 679.
    • (1999) Comprehensive Asymmetric Catalysis II , pp. 679
    • Aggarwal, V.K.1
  • 22
    • 0038758006 scopus 로고
    • Delmas and co-workers ( E. Borredon, F. Clavellinas, M. Delmas, A. Gaset and J. V. Sinisterra, J. Org. Chem., 1990, 55, 501) have shown that ester stabilised ylides can react with aldehydes when solid sodium carbonate is used as base. The solid hydrated form of the base is critical to its success as the reaction is believed to occur on its solid surface and requires the correct interstitial distance between the ions.
    • (1990) J. Org. Chem. , vol.55 , pp. 501
    • Borredon, E.1    Clavellinas, F.2    Delmas, M.3    Gaset, A.4    Sinisterra, J.V.5
  • 34
    • 0242503116 scopus 로고    scopus 로고
    • note
    • 3CN)) suggest that the energy difference between conformers 4A and 4B is ca. 20 kJ, which, if it was translated directly into epoxides, corresponds to 99.8% ee at 40°C).
  • 35
    • 0242419833 scopus 로고    scopus 로고
    • note
    • 3CN)) show that there is a 42° twist of the phenyl group in ylide conformer 4B resulting in reduced stabilization of the ylide carbanion.
  • 36
    • 0242671589 scopus 로고    scopus 로고
    • unpublished results
    • I. Bae, unpublished results.
    • Bae, I.1
  • 37
    • 0242503117 scopus 로고    scopus 로고
    • note
    • 64% Ee is observed for ylide 15 at 40°C, using the Boltzmann equation, it is predicted that the enantioselectivity should be 84% ee at -78°C. However, > 99% ee was actually observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.