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Volumn 129, Issue 5, 2007, Pages 1105-1112

Ring-expanding olefin metathesis: A route to highly active unsymmetrical macrocyclic oligomeric co-salen catalysts for the hydrolytic kinetic resolution of epoxides

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CONCENTRATION (PROCESS); HYDROLYSIS; MASS SPECTROMETRY; MONOMERS; OLIGOMERS; REACTION KINETICS;

EID: 33846783022     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0641406     Document Type: Article
Times cited : (132)

References (92)
  • 2
    • 0000496226 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Heidelberg
    • (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol. III, pp 1309-1326.
    • (1999) Comprehensive Asymmetric Catalysis I-III , vol.3 , pp. 1309-1326
    • Jacobsen, E.N.1    Wu, M.H.2
  • 14
    • 0001405437 scopus 로고
    • Wilkinsin, G, Stone, F. G. A, Abel, E. W, Hegedus, L. S, Eds, Pegamon: New York
    • (c) Jacobsen, E. N. In Comprehensive Organometallic Chemistry II; Wilkinsin, G., Stone, F. G. A., Abel, E. W., Hegedus, L. S., Eds.; Pegamon: New York, 1995; Vol. 12, pp 1097-1135.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 1097-1135
    • Jacobsen, E.N.1
  • 21
    • 0033419296 scopus 로고    scopus 로고
    • For recent reviews on salen chemistry, see: a
    • For recent reviews on salen chemistry, see: (a) Canali, L.; Sherrington, D. C. Chem. Soc. Rev. 1999, 28, 85-93.
    • (1999) Chem. Soc. Rev , vol.28 , pp. 85-93
    • Canali, L.1    Sherrington, D.C.2
  • 47
  • 64
    • 33846844667 scopus 로고    scopus 로고
    • The position of the ester functionality with respect to the macrocycles 4, 8 or polymers 9, 10 could be either 1,8- or 1,9-, as a result of the head-to-tail or head-to-head metathesis mode.
    • The position of the ester functionality with respect to the macrocycles 4, 8 or polymers 9, 10 could be either 1,8- or 1,9-, as a result of the head-to-tail or head-to-head metathesis mode.
  • 69
    • 0034746687 scopus 로고    scopus 로고
    • Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
    • (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
  • 80
    • 33846800843 scopus 로고    scopus 로고
    • Han, S.-Y.; Chang, S. In Handbook of Metathesis, 2 - Application in Organic Synthesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; pp 5-127.
    • (b) Han, S.-Y.; Chang, S. In Handbook of Metathesis, Vol. 2 - Application in Organic Synthesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; pp 5-127.
  • 87
    • 0038179667 scopus 로고    scopus 로고
    • Though NMR spectroseopy has been established as the standard method to investigate the kinetics of ROMP for example, see: Demel, S, Schoefberger, W, Slugovu, C, Stelzer, F. J. Mol. Catal. A: Chem. 2003, 200, 11-19, it fails to distinguish between oligomer 8 and polymer 9 in this case, which is required for estimating the rate of the backbiting cyclization
    • Though NMR spectroseopy has been established as the standard method to investigate the kinetics of ROMP (for example, see: Demel, S.; Schoefberger, W.; Slugovu, C.; Stelzer, F. J. Mol. Catal. A: Chem. 2003, 200, 11-19), it fails to distinguish between oligomer 8 and polymer 9 in this case, which is required for estimating the rate of the backbiting cyclization.
  • 89
    • 33846835814 scopus 로고    scopus 로고
    • If generated via the metallation of 8, complex 4 is almost Ru-free because of column chromatographic workup of 8. If generated via the metathesis of 3, complex 4 contains ca. 0.096% (w/w) residual Ru according to elemental analysis. In the HKR reactions, the results of catalysts prepared via the above two methods are almost identical. In control experiments using the HKR of epichlorohydrin, addition of 1.0 mol % of third generation Grubbs catalyst with respect to the Jacobsen catalyst 1 (X = OAc) exhibited negligible changes in catalytic performance.
    • If generated via the metallation of 8, complex 4 is almost Ru-free because of column chromatographic workup of 8. If generated via the metathesis of 3, complex 4 contains ca. 0.096% (w/w) residual Ru according to elemental analysis. In the HKR reactions, the results of catalysts prepared via the above two methods are almost identical. In control experiments using the HKR of epichlorohydrin, addition of 1.0 mol % of third generation Grubbs catalyst with respect to the Jacobsen catalyst 1 (X = OAc) exhibited negligible changes in catalytic performance.
  • 90
    • 33846802768 scopus 로고    scopus 로고
    • For a detailed study on the effect of counterions on the HKR, see ref 11
    • For a detailed study on the effect of counterions on the HKR, see ref 11.
  • 92
    • 0037664955 scopus 로고    scopus 로고
    • Schmalz, H.-G, Wirth, T, Eds, Wiley-VCH: Weinheim
    • (b) Metzger, J. O. In Organic Synthesis Highlights V; Schmalz, H.-G., Wirth, T., Eds.; Wiley-VCH: Weinheim, 2003: pp 82-92.
    • (2003) Organic Synthesis Highlights V , pp. 82-92
    • Metzger, J.O.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.