메뉴 건너뛰기




Volumn 12, Issue 5, 2010, Pages 1136-1138

Enantioselective friedel-crafts reaction of β-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; HELIOTRIDANE; PYRROLE DERIVATIVE; PYRROLIZIDINE ALKALOID;

EID: 77749280072     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100171z     Document Type: Article
Times cited : (84)

References (36)
  • 1
    • 77749272769 scopus 로고    scopus 로고
    • Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, L, Eds.; Wiley-Blackwell: West Sussex, 2008; pp 1-624.
    • (a) Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, L, Eds.; Wiley-Blackwell: West Sussex, 2008; pp 1-624.
  • 4
    • 2142648804 scopus 로고    scopus 로고
    • Georgii, G. F. Fluorine-Containing Heterocycles. Part I. Synthesis by Intramolecular Cyclization. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Elsevier: Amsterdam, 2004; 86, pp.129-224.
    • (b) Georgii, G. F. Fluorine-Containing Heterocycles. Part I. Synthesis by Intramolecular Cyclization. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Elsevier: Amsterdam, 2004; Vol. 86, pp.129-224.
  • 7
    • 65349147072 scopus 로고    scopus 로고
    • Selected examples of the catalytic asymmetric FC reaction with simple trifluoromethyl ketones: (a) Nie, J.; Zhang, G.-W.; Wang, L.; Fu, A.-P.; Zheng, Y,; Ma, J.-A. Chem. Commun. 2009, 2356-2358.
    • Selected examples of the catalytic asymmetric FC reaction with simple trifluoromethyl ketones: (a) Nie, J.; Zhang, G.-W.; Wang, L.; Fu, A.-P.; Zheng, Y,; Ma, J.-A. Chem. Commun. 2009, 2356-2358.
  • 9
    • 53849099614 scopus 로고    scopus 로고
    • With trifluoropyruvates: (c) Nakamura, S.; Hyodo, K.; Nakamura, Y.; Shibata, N.; Toru, T. Adv. Synth. Catal. 2008, 350, 1443-1448.
    • With trifluoropyruvates: (c) Nakamura, S.; Hyodo, K.; Nakamura, Y.; Shibata, N.; Toru, T. Adv. Synth. Catal. 2008, 350, 1443-1448.
  • 14
    • 77749272768 scopus 로고    scopus 로고
    • Wada, H. Japan Patent JP2005247788A, 2005.
    • (c) Wada, H. Japan Patent JP2005247788A, 2005.
  • 15
    • 84891022391 scopus 로고    scopus 로고
    • For reviews on asymmetric FC reaction, see: a, Bandini, M, Umani-Ronchi, A, Eds, WileyVCH: Weinheim
    • For reviews on asymmetric FC reaction, see: (a) Catalytic Asymmetric Friedel-Crafts Alkylations; Bandini, M., Umani-Ronchi, A., Eds.; WileyVCH: Weinheim, 2009; pp 1-301.
    • (2009) Catalytic Asymmetric Friedel-Crafts Alkylations , pp. 1-301
  • 17
    • 39749091670 scopus 로고    scopus 로고
    • Selected examples of asymmetric FC reaction of unprotected pyrrole: (a) Trost, B. M.; Müller, C. J. Am. Chem. Soc. 2008, 130, 2438-2439.
    • Selected examples of asymmetric FC reaction of unprotected pyrrole: (a) Trost, B. M.; Müller, C. J. Am. Chem. Soc. 2008, 130, 2438-2439.
  • 22
    • 84906427032 scopus 로고    scopus 로고
    • Katritzky, A. R, Ramsden, C. A, Scriven, E. F. V, Taylor, R. J. K, Eds, Elsevier Ltd, Oxford
    • (a) Troflmo, N. A.; Nedolya, N. A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier Ltd.: Oxford, 2008; Vol. 3, pp 45-268.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.3 , pp. 45-268
    • Troflmo, N.A.1    Nedolya, N.A.2
  • 26
    • 70349289167 scopus 로고    scopus 로고
    • Noritake, S.; Shibata, N.; Nomura, Y.; Huang, Y.-Y.; Matsnev, A.; Nakamura, S.; Toru, T.; Cahard, D. Org. Biomol. Chem. 2009, 7, 35993604.
    • (a) Noritake, S.; Shibata, N.; Nomura, Y.; Huang, Y.-Y.; Matsnev, A.; Nakamura, S.; Toru, T.; Cahard, D. Org. Biomol. Chem. 2009, 7, 35993604.
  • 29
    • 77749254126 scopus 로고    scopus 로고
    • The absolute configuration of 3b was assigned as S after derivatization to 4 and comparison of optical rotation to a sample of (R)-4 synthesized differently. See Supporting Information for details.
    • The absolute configuration of 3b was assigned as S after derivatization to 4 and comparison of optical rotation to a sample of (R)-4 synthesized differently. See Supporting Information for details.
  • 34
    • 33745683557 scopus 로고    scopus 로고
    • Selected examples: (a) Evans, D. A.; Fandrick, K. R. Org. Lett. 2006, 8, 2249-2252.
    • Selected examples: (a) Evans, D. A.; Fandrick, K. R. Org. Lett. 2006, 8, 2249-2252.
  • 36
    • 73949157419 scopus 로고    scopus 로고
    • Just before the submission of this manuscript, the asymmetric FC reaction of pyrroles was documented in the literature catalyzed by PYBOXDIPH-Zn(II) complexes. Singh, P. K.; Singh, V. K. Org. Lett. 2010, 12, 80-83.
    • Just before the submission of this manuscript, the asymmetric FC reaction of pyrroles was documented in the literature catalyzed by PYBOXDIPH-Zn(II) complexes. Singh, P. K.; Singh, V. K. Org. Lett. 2010, 12, 80-83.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.