메뉴 건너뛰기




Volumn 21, Issue 29, 2015, Pages 10443-10449

A Highly Efficient Chirality Switchable Synthesis of Dihydropyran-Fused Benzofurans by Fine-Tuning the Phenolic Proton of β-Isocupreidine (β-ICD) Catalyst with Methyl

Author keywords

chirality inversion; cycloadditions; density functional calculations; Lewis base; switchable enantioselectivity

Indexed keywords

CATALYSTS; CHIRALITY; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DESIGN FOR TESTABILITY; HYDROGEN BONDS; POLYOLS;

EID: 84934279190     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501145     Document Type: Article
Times cited : (22)

References (96)
  • 2
    • 77949627101 scopus 로고    scopus 로고
    • M. Bartõk, Chem. Rev. 2010, 110, 1663-1705.
    • (2010) Chem. Rev. , vol.110 , pp. 1663-1705
    • Bartõk, M.1
  • 4
    • 80051725623 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 5030-5034
    • (2011) Angew. Chem. , vol.123 , pp. 5030-5034
  • 7
    • 84870617615 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 5804-5808
    • (2012) Angew. Chem. , vol.124 , pp. 5804-5808
  • 11
    • 84902126932 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 9968-9972
    • (2013) Angew. Chem. , vol.125 , pp. 9968-9972
  • 13
    • 0033520752 scopus 로고    scopus 로고
    • For the pioneering work using β-ICD as an organocatalyst, see.
    • For the pioneering work using β-ICD as an organocatalyst, see:, Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219-10220.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10219-10220
    • Iwabuchi, Y.1    Nakatani, M.2    Yokoyama, N.3    Hatakeyama, S.4
  • 17
    • 49649083136 scopus 로고    scopus 로고
    • Y. C. Chen, Synlett 2008, 13, 1919-1930
    • (2008) Synlett , vol.13 , pp. 1919-1930
    • Chen, Y.C.1
  • 18
    • 77952363685 scopus 로고    scopus 로고
    • Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, C. E. Song, Ed, Wiley-VCH, Weinheim, Germany
    • Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, C. E. Song, Ed, Wiley-VCH, Weinheim, Germany, 2009
    • (2009)
  • 23
    • 84874254773 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 9886-9909
    • (2012) Angew. Chem. , vol.124 , pp. 9886-9909
  • 28
    • 18844451481 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 107-110
    • (2005) Angew. Chem. , vol.117 , pp. 107-110
  • 31
    • 33845211302 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 4407-4411
    • (2006) Angew. Chem. , vol.118 , pp. 4407-4411
  • 44
    • 84855763396 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 5468-5472
    • (2011) Angew. Chem. , vol.123 , pp. 5468-5472
  • 47
    • 84861537419 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 5473-5476
    • (2011) Angew. Chem. , vol.123 , pp. 5473-5476
  • 50
    • 84885669873 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 11490-11494
    • (2012) Angew. Chem. , vol.124 , pp. 11490-11494
  • 65
    • 84934338577 scopus 로고    scopus 로고
    • The absolute configuration of the [4+2] product was determined by the X-ray analysis of compound 3b. CCDC-951077 (3b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via. For details of the crystallographic data, please also see Table S3 in the Supporting Information.
    • The absolute configuration of the [4+2] product was determined by the X-ray analysis of compound 3b. CCDC-951077 (3b) 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. For details of the crystallographic data, please also see Table S3 in the Supporting Information.
  • 66
    • 84934338578 scopus 로고    scopus 로고
    • To reduce the computational cost, the calculation was for a methyl group instead of an ethyl group of allenoate. The experimental e.r. values of β-ICD and 5 -mediated reaction between (E)-3-(benzylidene)benzofuran-2-one and methyl allenoate were 95:5 and 13:87 respectively, which were obtained under identical conditions.
    • To reduce the computational cost, the calculation was for a methyl group instead of an ethyl group of allenoate. The experimental e.r. values of β-ICD and 5 -mediated reaction between (E)-3-(benzylidene)benzofuran-2-one and methyl allenoate were 95:5 and 13:87 respectively, which were obtained under identical conditions.
  • 67
    • 84934338579 scopus 로고    scopus 로고
    • During the preparation of this manuscript, two computational studies of achiral Lewis base catalyzed cycloaddition of allenoates were reported, see
    • During the preparation of this manuscript, two computational studies of achiral Lewis base catalyzed cycloaddition of allenoates were reported, see
  • 71
    • 82155195150 scopus 로고    scopus 로고
    • For selected examples, see
    • T. Marcelli, WIREs Comput. Mol. Sci. 2011, 1, 142-152. For selected examples, see
    • (2011) WIREs Comput. Mol. Sci. , vol.1 , pp. 142-152
    • Marcelli, T.1
  • 89
    • 84934338580 scopus 로고    scopus 로고
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A., Jr., Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2009
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A., Jr., Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
  • 90
    • 84934338581 scopus 로고    scopus 로고
    • CYLview, 1.0b; Legault, C. Y. Université de Sherbrooke, 2009
    • CYLview, 1.0b; Legault, C. Y. Université de Sherbrooke, 2009. (http://www.cylview.org).
  • 96
    • 0344887064 scopus 로고
    • More acidic CF3CH2OH completely inhibited the reaction probably due to the acid-base quench of the active catalyst. For pKa values of alcohols, see.
    • More acidic CF3CH2OH completely inhibited the reaction probably due to the acid-base quench of the active catalyst. For pKa values of alcohols, see:, F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 456-463
    • Bordwell, F.G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.