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Volumn 61, Issue 26, 2005, Pages 6180-6185

Consecutive Rh(I)-catalyzed Alder-ene/Diels-Alder/Diels-Alder reaction sequence affording rapid entry to polycyclic compounds

Author keywords

Allenynes; Consecutive transition metal catalyzed reactions; Cross conjugated trienes; Diels Alder reaction; Polycycles; Rh(I) allenic Alder ene

Indexed keywords

ALKADIENE; ALKENE; ALKYNE DERIVATIVE; CARBON; POLYCYCLIC HYDROCARBON; RHODIUM DERIVATIVE; TRANSITION ELEMENT;

EID: 20444476185     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.141     Document Type: Article
Times cited : (58)

References (33)
  • 12
    • 0030599225 scopus 로고    scopus 로고
    • Cross-conjugated trienes have been accessed previously using transition metal mediation. Malacria has subjected an allenyne to a cobalt(I) complex and obtained a mixture of two cross-conjugated trienes by using a tert-butyl group on the proximal double bond of the allene to direct the regiochemistry of the cyclization reaction to the distal double bond of the allene. (a) D. Lierena, C. Aubert, and M. Malacria Tetrahedron Lett. 37 1996 7027
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7027
    • Lierena, D.1    Aubert, C.2    Malacria, M.3
  • 13
    • 0032190825 scopus 로고    scopus 로고
    • Sato has effected an Alder-ene reaction from an allenynol by using a two-carbon tether that favors reaction with the distal double bond of the allene. (b) T. Yamazaki, H. Urabe, and F. Sato Tetrahedron Lett. 39 1998 7333
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7333
    • Yamazaki, T.1    Urabe, H.2    Sato, F.3
  • 15
    • 20444468298 scopus 로고    scopus 로고
    • note
    • To the best of our knowledge, this type of Ireland-Claisen rearrangement is an unprecedented protocol for the formation of allenes.
  • 16
    • 20444457383 scopus 로고    scopus 로고
    • note
    • More recently our group has found that performing Alder-ene reactions at lower concentrations (0.05-0.01 M) gives higher yields of trienes in faster reaction times suggesting product inhibition.
  • 17
    • 0032567381 scopus 로고    scopus 로고
    • For references regarding rhodium(I) transition metal catalyzed [4+2] cycloaddition reactions between electronically similar dienes and dienophiles, see: S.R. Gilbertson, G.S. Hoge, and D.G. Genov J. Org. Chem. 63 1998 10077
    • (1998) J. Org. Chem. , vol.63 , pp. 10077
    • Gilbertson, S.R.1    Hoge, G.S.2    Genov, D.G.3
  • 26
    • 20444502732 scopus 로고    scopus 로고
    • note
    • - gave no reaction.
  • 27
    • 0032499035 scopus 로고    scopus 로고
    • A few groups have reported rhodium catalyzed formal [4+2] reactions using alkenes as the dienophile to form fused [6-5] ring systems. (a) S.R. Gilbertson, and G.S. Hoge Tetrahedron Lett. 39 1998 2075
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2075
    • Gilbertson, S.R.1    Hoge, G.S.2
  • 30
    • 20444505403 scopus 로고    scopus 로고
    • note
    • - for the one pot process. Compare the results of Table 3 and Scheme 3.
  • 32
    • 20444460948 scopus 로고    scopus 로고
    • note
    • The X-ray crystallographic data have been included in the supporting information as a CIF file and have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 256297 and 256298.
  • 33
    • 4544376543 scopus 로고    scopus 로고
    • For a recent review on using a single catalyst to mediate two or more reactions, see: A. Ajamian, and J.L. Gleason Angew. Chem., Int. Ed. 43 2004 3754
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3754
    • Ajamian, A.1    Gleason, J.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.