메뉴 건너뛰기




Volumn , Issue 22, 2013, Pages 4836-4843

Bifunctional primary amine-squaramide catalyzed enantioselective intramolecular Michael addition of keto-enones: A convenient process to the stereocontrolled construction of trans-dihydrobenzofuran skeletons

Author keywords

Asymmetric catalysis; Diastereoselectivity; Enantioselectivity; Michael addition; Oxygen heterocycles; Synthetic methods

Indexed keywords


EID: 84880937834     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300331     Document Type: Article
Times cited : (32)

References (59)
  • 1
  • 9
    • 0346753438 scopus 로고    scopus 로고
    • for selected recent examples, see
    • M. Sefkow, Synthesis 2003, 2595-2625; for selected recent examples, see
    • (2003) Synthesis , pp. 2595-2625
    • Sefkow, M.1
  • 16
    • 84856998244 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 1710-1713.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1710-1713
  • 17
    • 33747233073 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5194 - 5197
    • S. Kaiser, S. P. Smidt, A. Pfaltz, Angew. Chem. 2006, 118, 5318; Angew. Chem. Int. Ed. 2006, 45, 5194-5197.
    • (2006) Angew. Chem. , vol.118 , pp. 5318
    • Kaiser, S.1    Smidt, S.P.2    Pfaltz, A.3
  • 27
    • 55049138759 scopus 로고    scopus 로고
    • P. I. Dalko (Ed.), Wiley-VCH, Weinheim, Germany
    • P. I. Dalko (Ed.), Enantioselective Organocatalysis, Wiley-VCH, Weinheim, Germany, 2007.
    • (2007) Enantioselective Organocatalysis
  • 28
    • 84871997136 scopus 로고    scopus 로고
    • For recent general reviews about asymmetric organocatalysis, see: a) J. Alemán, S. Cabrera, Chem. Soc. Rev. 2013, 42, 774-793.
    • (2013) Chem. Soc. Rev. , vol.42 , pp. 774-793
    • Alemán, J.1    Cabrera, S.2
  • 33
    • 48849094479 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4638 - 4660
    • A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716; Angew. Chem. Int. Ed. 2008, 47, 4638-4660.
    • (2008) Angew. Chem. , vol.120 , pp. 4716
    • Dondoni, A.1    Massi, A.2
  • 34
    • 52149113820 scopus 로고    scopus 로고
    • D. W. C. MacMillan, for a recent general review about asymmetric organocatalytic cyclization and cycloaddition reactions, see
    • D. W. C. MacMillan, Nature 2008, 455, 304-308; for a recent general review about asymmetric organocatalytic cyclization and cycloaddition reactions, see
    • (2008) Nature , vol.455 , pp. 304-308
  • 44
    • 84874225572 scopus 로고    scopus 로고
    • Over course of this study, Jørgensen reported a quinidine-based primary amine catalyzed intramolecular Michael addition of ketones to enones to generate optically active 2,3-disubstituted cis-2,3-dihydrobenzofurans with high levels of enantioselectivity, but with only moderate diastereoselectivity. For details, see:, Ł. Albrecht
    • Over course of this study, Jørgensen reported a quinidine-based primary amine catalyzed intramolecular Michael addition of ketones to enones to generate optically active 2,3-disubstituted cis-2,3-dihydrobenzofurans with high levels of enantioselectivity, but with only moderate diastereoselectivity. For details, see:, J. Christensen, Ł. Albrecht, K. A. Jørgensen, Chem. Asian J. 2013, 8, 648-652.
    • (2013) Chem. Asian J. , vol.8 , pp. 648-652
    • Christensen, J.1    Jørgensen, K.A.2
  • 45
    • 84884607357 scopus 로고    scopus 로고
    • New Strategies
    • (Ed.:, B. Pignataro), Wiley-VCH, Weinheim, Germany
    • For reviews about chiral thiourea catalysts, see: a) E. Marques-Lopez, R. P. Herrera, in: New Strategies, in: Chemical Synthesis and Catalysis (Ed.:, B. Pignataro), Wiley-VCH, Weinheim, Germany, 2012, p. 175-199.
    • (2012) Chemical Synthesis and Catalysis , pp. 175-199
    • Marques-Lopez, E.1    Herrera, R.P.2
  • 58
    • 79958185446 scopus 로고    scopus 로고
    • For a review about squaramide-based organocatalysis, see
    • For a review about squaramide-based organocatalysis, see:, J. Alemán, A. Parra, H. Jiang, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 6890-6899.
    • (2011) Chem. Eur. J. , vol.17 , pp. 6890-6899
    • Alemán, J.1    Parra, A.2    Jiang, H.3    Jørgensen, K.A.4
  • 59
    • 84880933430 scopus 로고    scopus 로고
    • CCDC-931250 (for 5a) 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.