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Volumn 124, Issue 38, 2002, Pages 11292-11294

Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; VINDOLINE;

EID: 0037174410     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027533n     Document Type: Article
Times cited : (127)

References (33)
  • 27
    • 0032488853 scopus 로고    scopus 로고
    • note
    • Padwa, A.; Price, A. T. J. Org. Chem. 1998, 63, 556 and 1995, 60, 6258. Interestingly, this endo diastereoselection is unique to the intramolecular 1,3-dipolar cycloaddition and intermolecular reactions proceed with indole exo cycloaddition directed to an analogous α-face, see: Muthusamy, S.; Gunanathan, C.; Babu, S. A. Tetrahedron Lett. 2001, 42, 523. The endo diastereoselection observed herein may be attributed simply to a conformational (strain) preference dictated by the dipolarophile tether since it mirrors the relative energy of the four possible products α-face endo < β-face endo ΔE = 5.2 kcal/mol < α-face exo ΔE = 13.1 kcal/mol < β-face exo ΔE = 151 kcal/mol for 14a, MM2 force field).
  • 28
    • 0010421175 scopus 로고    scopus 로고
    • note
    • Stereochemical assignments for 16b and 17b have been confirmed by X-ray of the analogous products bearing an indole C6 methoxy substitutent.
  • 29
    • 0010501363 scopus 로고    scopus 로고
    • note
    • The X-ray crystal structure of 21b has been deposited with the Cambridge Crystallographic Data Centre under the deposition number CCDC 186237.
  • 30
    • 0010421034 scopus 로고    scopus 로고
    • note
    • 2 detection or isolation.
  • 33
    • 0010421315 scopus 로고
    • and refs cited therein
    • For additional examples of allene > alkyne intramolecular Diels-Alders reactions, see: Kanematsu, K. Rev. Heteroat. Chem. 1993, 9, 213 and refs cited therein.
    • (1993) Rev. Heteroat. Chem. , vol.9 , pp. 213
    • Kanematsu, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.