메뉴 건너뛰기




Volumn 46, Issue 12, 2007, Pages 1983-1987

Enantioselective organocatalytic conjugate addition of N heterocycles to α,β-unsaturated aldehydes

Author keywords

Aldehydes; Asymmetric synthesis; Density functional calculations; Nitrogen heterocycles; Organocatalysis

Indexed keywords

DENSITY FUNCTIONAL THEORY; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

EID: 34250157969     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604854     Document Type: Article
Times cited : (182)

References (80)
  • 1
    • 11144263200 scopus 로고    scopus 로고
    • See, for example: a
    • See, for example: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
    • (2004) Angew. Chem , vol.116 , pp. 5248
    • Dalko, P.I.1    Moisan, L.2
  • 2
  • 5
    • 27344444510 scopus 로고    scopus 로고
    • Special Issue: Asymmetric Organocatalysis
    • d) "Special Issue: Asymmetric Organocatalysis", Acc. Chem. Res. 2004, 37.
    • (2004) Acc. Chem. Res , vol.37
  • 12
    • 20444441594 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3703;
    • (2005) Chem. Int. Ed , vol.44 , pp. 3703
    • Angew1
  • 14
    • 20444494428 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3706;
    • (2005) Chem. Int. Ed , vol.44 , pp. 3706
    • Angew1
  • 21
  • 25
  • 27
  • 43
  • 51
  • 59
  • 62
  • 65
    • 18044395960 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2393.
    • (2005) Chem. Int. Ed , vol.44 , pp. 2393
    • Angew1
  • 68
    • 33845505476 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7876.
    • (2006) Chem. Int. Ed , vol.45 , pp. 7876
    • Angew1
  • 69
    • 34250884158 scopus 로고    scopus 로고
    • -1, colorless crystals. CCDC-631156 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.
    • -1, colorless crystals. CCDC-631156 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.
  • 70
    • 34250864738 scopus 로고    scopus 로고
    • Gaussian 03 Revision A.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. C
    • Gaussian 03 (Revision A.1), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 2003.
  • 75
    • 34250827525 scopus 로고    scopus 로고
    • Additon of 1,2,4-triazole from the Re face to iminium ion (E)-12, derived from catalyst 3 and 2-pentenal (2a), leads to the product 4a with R configuration. The X-ray analysis of compound 7c, originating from the reaction between 5-phenyltetrazole and 4-methylpent-2-enal (4d), gave a product with S configuration. The reason for the change of chirality is a result of a change in priority between the substituents, and the S configuration of 7c is also consistent with addition from the Re face of iminium ion (E)-12.
    • Additon of 1,2,4-triazole from the Re face to iminium ion (E)-12, derived from catalyst 3 and 2-pentenal (2a), leads to the product 4a with R configuration. The X-ray analysis of compound 7c, originating from the reaction between 5-phenyltetrazole and 4-methylpent-2-enal (4d), gave a product with S configuration. The reason for the "change" of chirality is a result of a change in priority between the substituents, and the S configuration of 7c is also consistent with addition from the Re face of iminium ion (E)-12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.