메뉴 건너뛰기




Volumn 44, Issue 4, 2005, Pages 609-612

Direct coupling of pyrroles with carbonyl compounds: Short enantioselective synthesis of (S)-ketorolac

Author keywords

C C coupling; Copper; Enantioselectivity; Heterocycles; Total synthesis

Indexed keywords

CARBONYLATION; DRUG PRODUCTS; ESTERS; SYNTHESIS (CHEMICAL);

EID: 13244269968     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462048     Document Type: Article
Times cited : (155)

References (30)
  • 3
    • 0013319981 scopus 로고    scopus 로고
    • b) A. F. Littke, G. C. Fu, Angew. Chem, 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211, and references therein.
    • (2002) Angew. Chem. , vol.114 , pp. 4350-4386
    • Littke, A.F.1    Fu, G.C.2
  • 4
    • 0037112673 scopus 로고    scopus 로고
    • and references therein
    • b) A. F. Littke, G. C. Fu, Angew. Chem, 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211, and references therein.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4176-4211
  • 5
    • 0000324324 scopus 로고    scopus 로고
    • a) For a review of metal-mediated couplings of this type, see: M. Miura, M. Nomura, Top. Curr. Chem. 2002, 219, 211-241;
    • (2002) Top. Curr. Chem. , vol.219 , pp. 211-241
    • Miura, M.1    Nomura, M.2
  • 6
    • 0042856823 scopus 로고    scopus 로고
    • and references therein
    • b) For recent advances in this area, see: B. Sezen, D. Sames, J. Am. Chem. Soc. 2003, 125, 10580-10585, and references therein;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10580-10585
    • Sezen, B.1    Sames, D.2
  • 7
    • 0037393778 scopus 로고    scopus 로고
    • c) For a review of palladium-mediated α-arylation of enolates, see: D. A. Culkin, J. F. Hartwig, Acc. Chem. Res. 2003, 36, 234-245.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 234-245
    • Culkin, D.A.1    Hartwig, J.F.2
  • 9
    • 4544376553 scopus 로고    scopus 로고
    • and references therein
    • T. Tsuchimoto, Y. Ozawa, R. Negoro, E. Shirakawa, Y. Kawakami, Angew. Chem. 2004, 116, 4327-4329; Angew. Chem. Int. Ed. 2004, 43, 4231-4233, and references therein.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4231-4233
  • 11
    • 0345834040 scopus 로고
    • For an authoritative review of Syntex's landmark discovery and the development of ketorolac, see: J. M. Muchowski, Adv. Med. Chem, 1992, 1, 109-135.
    • (1992) Adv. Med. Chem , vol.1 , pp. 109-135
    • Muchowski, J.M.1
  • 14
    • 0000298944 scopus 로고
    • a) One practical path to enantiopure (S)-1 uses enzymatic kinetic resolution (92% yield, 85% ee), see: G. Fulling, C. J. Sih, J. Am. Chem. Soc. 1987, 109, 2845-2846;
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2845-2846
    • Fulling, G.1    Sih, C.J.2
  • 17
    • 0000048258 scopus 로고
    • (Eds.: B. M. Trost, I. Flemming), Pergamon, Oxford
    • W. Oppolzer in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Flemming), Pergamon, Oxford, 1991, pp. 315-399.
    • (1991) Comprehensive Organic Synthesis, Vol. 5 , vol.5 , pp. 315-399
    • Oppolzer, W.1
  • 19
    • 0001004311 scopus 로고    scopus 로고
    • b) U. Jahn, J. Org. Chem. 1998, 63, 7130-7131;
    • (1998) J. Org. Chem. , vol.63 , pp. 7130-7131
    • Jahn, U.1
  • 26
    • 0026440164 scopus 로고
    • D. R. Artis, I.-S. Cho, J. M. Muchowski, Can. J. Chem. 1992, 70, 1838-1842. This paper reports the oxidative cyclization of a malonate onto a pyrrole. Such a strategy would obviously not be amenable to an enantioselective variant and it requires decarboxylation of the extraneous carboxyl group. For a related approach using a carbenoid generated from a diazoketone, see: P. Müller, P. Pholleux, Helv. Chim. Acta 1998, 81, 317-323.
    • (1992) Can. J. Chem. , vol.70 , pp. 1838-1842
    • Artis, D.R.1    Cho, I.-S.2    Muchowski, J.M.3
  • 27
    • 0032481301 scopus 로고    scopus 로고
    • D. R. Artis, I.-S. Cho, J. M. Muchowski, Can. J. Chem. 1992, 70, 1838-1842. This paper reports the oxidative cyclization of a malonate onto a pyrrole. Such a strategy would obviously not be amenable to an enantioselective variant and it requires decarboxylation of the extraneous carboxyl group. For a related approach using a carbenoid generated from a diazoketone, see: P. Müller, P. Pholleux, Helv. Chim. Acta 1998, 81, 317-323.
    • (1998) Helv. Chim. Acta , vol.81 , pp. 317-323
    • Müller, P.1    Pholleux, P.2
  • 30
    • 13244283660 scopus 로고    scopus 로고
    • Detailed experimental procedures, copies of all spectral data and full characterization are contained in the Supporting Information. CCDC 251395 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif..


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.