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Volumn 64, Issue 2, 1999, Pages 340-341

Double annulation route to highly substituted and functionalized trans- fused bicyclic compounds

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; DECALIN DERIVATIVE;

EID: 0033593542     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9822737     Document Type: Article
Times cited : (28)

References (40)
  • 5
    • 0002404267 scopus 로고
    • Rodrigo, R. G. A., Ed.; Academic Press: New York, Chapter 2
    • Pelletier, S. W.; Mody, N. V. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18, Chapter 2, p 99-216.
    • (1981) The Alkaloids , vol.18 , pp. 99-216
    • Pelletier, S.W.1    Mody, N.V.2
  • 23
    • 0003887404 scopus 로고
    • Harper & Row: New York
    • ΔΔG ° = 1.30 kcal/mol for the two chair conformers of methyl cyclohexanecarboxylate, while ΔΔG ° = 0.24 kcal/mol for the two chair conformers of cyclohexanecarbonitrile. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987.
    • (1987) Mechanism and Theory in Organic Chemistry, 3rd Ed.
    • Lowry, T.H.1    Richardson, K.S.2
  • 25
    • 0344072293 scopus 로고    scopus 로고
    • note
    • s-symmetric diastereomer (not shown) could be isolated when the double Michael reaction was carried out at room temperature.
  • 27
    • 0345365729 scopus 로고    scopus 로고
    • note
    • Compound 4b can only have a trans ring fusion. If 4b′, 4c, or 4e had a cis ring fusion, the methine H would be equatorial with respect to the B ring in the lower-energy conformer, and a smaller coupling constant to the vicinal trans H would be expected.
  • 31
    • 0345365728 scopus 로고    scopus 로고
    • note
    • A wide variety of other conditions have also been explored, but the Dieckmann product of 3d has never been obtained in good, reproducible yield.
  • 32
    • 0345365727 scopus 로고    scopus 로고
    • note
    • The stereochemistry was confirmed by coupling constant analysis and a NOESY experiment.
  • 38
    • 0344934313 scopus 로고    scopus 로고
    • note
    • Preliminary results suggest that the double Michael reaction proceeds with ketoester, cyano ketone, and nitroalkane nucleophiles and with alkynoate and internal alkynone electrophiles.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.