메뉴 건너뛰기




Volumn , Issue 29, 2013, Pages 6535-6539

Electrostatic repulsion and hydrogen-bonding interactions in a simple N-aryl-L-valinamide organocatalyst control the stereoselectivity in asymmetric aldol reactions

Author keywords

Aldol reactions; Asymmetric catalysis; Heterocycles; Organocatalysis; Synthetic methods

Indexed keywords


EID: 84885583094     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201301138     Document Type: Article
Times cited : (30)

References (106)
  • 3
    • 77950261392 scopus 로고    scopus 로고
    • B. List (Ed.), Springer, Berlin
    • B. List (Ed.), Asymmetric Organocatalysis, Springer, Berlin, 2009.
    • (2009) Asymmetric Organocatalysis
  • 37
    • 70350616302 scopus 로고    scopus 로고
    • K. Maruoka (Ed.), Wiley-VCH, Weinheim, Germany
    • K. Maruoka (Ed.), Asymmetric Phase Transfer Catalysis, Wiley-VCH, Weinheim, Germany, 2008.
    • (2008) Asymmetric Phase Transfer Catalysis
  • 54
    • 84872750140 scopus 로고    scopus 로고
    • Nugent) T.C. in: (Ed.:, Wiley-VCH, Weinheim, Germany
    • P. KočovskÃ, S. Stončius, in: Chiral Amine Synthesis (Ed.:, T. C. Nugent), Wiley-VCH, Weinheim, Germany, 2010, pp. 131-156.
    • (2010) Chiral Amine Synthesis , pp. 131-156
    • Kočovskã, P.1    Stončius, S.2
  • 60
    • 11844259698 scopus 로고    scopus 로고
    • R. Mahrwald (Ed.), Wiley-VCH, Weinheim, Germany
    • R. Mahrwald (Ed.), Modern Aldol Reactions, Wiley-VCH, Weinheim, Germany, 2004, vol. 1 and 2.
    • (2004) Modern Aldol Reactions , vol.1-2
  • 72
    • 60849085172 scopus 로고    scopus 로고
    • The single-crystal X-ray analysis of perfluorophenyl-N-prolinamide was reported, in which the stereoselectivity of the aldol product was attributed to the enhanced NH acidity and conformation of the perfluorophenyl ring; for details, see:, J. N. Moorthy, S. Saha, Eur. J. Org. Chem. 2009, 739.
    • (2009) Eur. J. Org. Chem. , pp. 739
    • Moorthy, J.N.1    Saha, S.2
  • 92
    • 79959190033 scopus 로고    scopus 로고
    • Gaussian, Inc., Wallingford, CT
    • 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. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, 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, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision C.01, Gaussian, Inc., Wallingford, CT, 2009.
    • (2009) Gaussian 09, Revision C.01
    • Frisch, M.J.1
  • 105
    • 84877731723 scopus 로고    scopus 로고
    • During the course of our study, the preparation of the (2'S,3R) isomer was reported; however, the ee was 82 % (syn/anti = 93:7), see:, A. Kumar, S. S. Chimni, Tetrahedron 2013, 69, 5197.
    • (2013) Tetrahedron , vol.69 , pp. 5197
    • Kumar, A.1    Chimni, S.S.2
  • 106
    • 84885603928 scopus 로고    scopus 로고
    • CCDC-941823 (for 6b) 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. See also the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.