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Volumn 71, Issue 5, 2006, Pages 2192-2195

Asymmetric Diels-Alder reactions of chiral cyclopropylidene imide dienophiles: Preparation of gem-dimethyl- and spirocyclopropane norbornyl carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

GEM-DIMETHYL; N-ACYLOXAZOLIDINONES; RAPID ASYMMETRIC SYNTHESIS;

EID: 33644661045     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052516c     Document Type: Article
Times cited : (25)

References (29)
  • 1
    • 0000097153 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, and references therein
    • For recent reviews of enantioselective Diels-Alder reactions, see: (a) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 3, p 1177 and references therein.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1177
    • Evans, D.A.1    Johnson, J.S.2
  • 2
    • 0003417469 scopus 로고
    • Trust, B. M., Ed.; Pergamon Press: New York
    • (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trust, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5.
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Oppolzer, W.1
  • 10
  • 12
    • 33644655338 scopus 로고    scopus 로고
    • special issue on organocatalysis
    • (d) Acc. Chem. Res. 2004, 37 (8) (special issue on organocatalysis).
    • (2004) Acc. Chem. Res. , vol.37 , Issue.8
  • 17
    • 0029087822 scopus 로고
    • The enantiomer of acid 5 has been reported to have cytotoxic effects on cancer cell lines, see: Jaeger, W.; Paesler, B.; Buchgauer, G.; Chiba, P. Pharmazie 1995, 50, 619.
    • (1995) Pharmazie , vol.50 , pp. 619
    • Jaeger, W.1    Paesler, B.2    Buchgauer, G.3    Chiba, P.4
  • 18
    • 0001487604 scopus 로고    scopus 로고
    • For a review on the synthesis of various alkylidenecyclopropanes, see: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
    • (1998) Chem. Rev. , vol.98 , pp. 589
    • Brandi, A.1    Goti, A.2
  • 25
    • 33644661523 scopus 로고    scopus 로고
    • note
    • The assignment of products 13-15, which were not isolated, was based on NMR experiments on the crude reaction mixture.
  • 26
    • 33644639182 scopus 로고    scopus 로고
    • note
    • See the Supporting Information.
  • 28
    • 84971070066 scopus 로고
    • For catalytic hydrogenation of a similar spirocyclopropyl norbornyl system, see: Gream, G. E.; Pincombe, C. F. Aust. J. Chem. 1974, 27, 543.
    • (1974) Aust. J. Chem. , vol.27 , pp. 543
    • Gream, G.E.1    Pincombe, C.F.2
  • 29
    • 33644661666 scopus 로고    scopus 로고
    • note
    • No attempt was made to isolate the individual diastereomers, and structural assignments were based on NMR experiments and analogy to products 13-15.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.