메뉴 건너뛰기




Volumn , Issue 12, 2003, Pages 1910-1914

The First Organocatalytic Hetero-Domino Knoevenagel-Diels-Alder-Epimerization Reactions: Diastereoselective Synthesis of Highly Substituted Spiro[cyclohexane-1,2′-indan]-1′,3′ ,4-triones

Author keywords

2 amino 1,3 butadiene; Diels Alder reaction; Domino reactions; Organic Lewis acid; Organocatalysis

Indexed keywords

1,3 INDANDIONE DERIVATIVE; ALDEHYDE DERIVATIVE; CYCLOHEXANE DERIVATIVE; PROLINE; PYRROLIDINE DERIVATIVE; QUINONE DERIVATIVE;

EID: 0142059749     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41486     Document Type: Article
Times cited : (115)

References (58)
  • 6
    • 0000097153 scopus 로고    scopus 로고
    • Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York
    • (a) Evans, D. A.; Johnson, J. S. Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999, 1177.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1177
    • Evans, D.A.1    Johnson, J.S.2
  • 11
    • 0032473509 scopus 로고    scopus 로고
    • (e) Corey, E. J.; Perez, A. G. Angew. Chem. Int. Ed. 1998, 37, 388; Angew. Chem. 1998, 110, 402.
    • (1998) Angew. Chem. , vol.110 , pp. 402
  • 48
    • 84989487596 scopus 로고
    • (f) Kuck, D. Chem. Ber. 1994, 127, 409.
    • (1994) Chem. Ber. , vol.127 , pp. 409
    • Kuck, D.1
  • 53
    • 0142133297 scopus 로고    scopus 로고
    • note
    • + 403.1305.
  • 54
    • 0142133296 scopus 로고    scopus 로고
    • note
    • Formation of the kinetic product, trans-spirane 6aa as the major isomer in ionic liquids, as opposed to the cis-spirane 5aa through the endo-transition state in the classical Diels-Alder route is likely explained by unique solvation in the ionic liquid of the 2-amino-1,3-butadiene 9a and dienophile 8a in the transition states shown below. Asymmetric solvation in the ionic liquids may produce a steric hindrance with the phenyl group on the dienophile, in the endotransition state, thereby disfavoring it (Figure 1). equation presented
  • 56
    • 0000201762 scopus 로고
    • The Knoevenagel Reaction
    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, Chap. 1.11
    • (b) Tietze, L. F.; Beifuss, U. The Knoevenagel Reaction, In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Chap. 1.11, 341-392.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 341-392
    • Tietze, L.F.1    Beifuss, U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.