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Volumn 2, Issue 4, 2011, Pages 633-637

Gold(I)-catalyzed intermolecular (4 + 2) cycloaddition of allenamides and acyclic dienes

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC DIENES; ALLENAMIDES; CONJUGATED DIENES; CYCLOHEXENES; DIASTEREO-SELECTIVITY; DIELS-ALDER; GOLD-CATALYZED REACTIONS;

EID: 79955576875     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c0sc00630k     Document Type: Article
Times cited : (78)

References (47)
  • 8
    • 0142213273 scopus 로고    scopus 로고
    • For a review on the synthetic utility of allenamides, see
    • For a review on the synthetic utility of allenamides, see: L.-L. Wei, H. Xiong and R. P. Hsung, Acc. Chem. Res., 2003, 36, 773.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 773
    • Wei, L.-L.1    Xiong, H.2    Hsung, R.P.3
  • 9
    • 77955134646 scopus 로고    scopus 로고
    • For other types of Au-catalyzed reactions of allenamides, see
    • For other types of Au-catalyzed reactions of allenamides, see: A. W. Hill, M. R. J. Elsegood and M. C. Kimber, J. Org. Chem., 2010, 75, 5406
    • (2010) J. Org. Chem. , vol.75 , pp. 5406
    • Hill, A.W.1    Elsegood, M.R.J.2    Kimber, M.C.3
  • 11
    • 0031708442 scopus 로고    scopus 로고
    • For a Rh-catalyzed intermolecular cycloaddition between unactivated vinylallenes (4C) and alkynes (2C), see
    • For a Rh-catalyzed intermolecular cycloaddition between unactivated vinylallenes (4C) and alkynes (2C), see: M. Murakami, M. Ubukata, K. Itami and Y. Ito, Angew. Chem., Int. Ed., 1998, 37, 2248.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2248
    • Murakami, M.1    Ubukata, M.2    Itami, K.3    Ito, Y.4
  • 12
    • 70450190983 scopus 로고    scopus 로고
    • We are only aware of a Pt-catalyzed (3 + 2) cycloaddition of allenyl silyl ethers and enol ethers, see
    • We are only aware of a Pt-catalyzed (3 + 2) cycloaddition of allenyl silyl ethers and enol ethers, see: H. Kusama, M. Ebisawa, H. Funami and N. Iwasawa, J. Am. Chem. Soc., 2009, 131, 16352.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16352
    • Kusama, H.1    Ebisawa, M.2    Funami, H.3    Iwasawa, N.4
  • 13
    • 70350496890 scopus 로고    scopus 로고
    • For recent reviews on Au-and Pt-catalyzed reactions, see
    • For recent reviews on Au-and Pt-catalyzed reactions, see: A. Fürstner, Chem. Soc. Rev., 2009, 38, 3208
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 3208
    • Fürstner, A.1
  • 17
    • 69949147971 scopus 로고    scopus 로고
    • Allenes and dienes may react in several ways in the presence of Au catalysts. For instance, we have shown that allenes can behave as 2C or 3C atom partners in their gold-catalyzed intramolecular cycloadditions with dienes, see, and
    • Allenes and dienes may react in several ways in the presence of Au catalysts. For instance, we have shown that allenes can behave as 2C or 3C atom partners in their gold-catalyzed intramolecular cycloadditions with dienes, see P. Mauleón, R. M. Zeldin, A. Z. González and F. D. Toste, J. Am. Chem. Soc., 2009, 131, 6348, and
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 6348
    • Mauleón, P.1    Zeldin, R.M.2    González, A.Z.3    Toste, F.D.4
  • 23
    • 79955581371 scopus 로고    scopus 로고
    • note
    • See the Supplementary Information† for more details.
  • 24
    • 0033578602 scopus 로고    scopus 로고
    • It has been shown that allenamides can participate in uncatalyzed hetero-(4 + 2) inverse electron demand Diels-Alder cycloadditions, see
    • It has been shown that allenamides can participate in uncatalyzed hetero-(4 + 2) inverse electron demand Diels-Alder cycloadditions, see: L.-L. Wei, H. Xiong, C. J. Douglas and R. P. Hsung, Tetrahedron Lett., 1999, 40, 6903
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6903
    • Wei, L.-L.1    Xiong, H.2    Douglas, C.J.3    Hsung, R.P.4
  • 29
    • 0038616368 scopus 로고    scopus 로고
    • Two specific examples of normal electron demand (4 + 2) reactions have also been reported, see
    • Two specific examples of normal electron demand (4 + 2) reactions have also been reported, see: J. P. Bacci, K. L. Greenman and D. L. Van Vranken, J. Org. Chem., 2003, 68, 4955
    • (2003) J. Org. Chem. , vol.68 , pp. 4955
    • Bacci, J.P.1    Greenman, K.L.2    van Vranken, D.L.3
  • 31
    • 0030726933 scopus 로고    scopus 로고
    • For other types of (2 + 2) cycloadditions employing different allenamides, see
    • For other types of (2 + 2) cycloadditions employing different allenamides, see: M. Kimura, Y. Horino, Y. Wakamiya, T. Okayima and Y. Tamaru, J. Am. Chem. Soc., 1997, 119, 10869.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10869
    • Kimura, M.1    Horino, Y.2    Wakamiya, Y.3    Okayima, T.4    Tamaru, Y.5
  • 32
    • 77950224470 scopus 로고    scopus 로고
    • For Au-catalyzed intramolecular (2 + 2) cycloadditions of allenetethered alkenes, see
    • For Au-catalyzed intramolecular (2 + 2) cycloadditions of allenetethered alkenes, see M. Alcarazo, T. Stork, A. Anoop, W. Thiel and A. Furstner, Angew. Chem., Int. Ed., 2010, 49, 2542.
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 2542
    • Alcarazo, M.1    Stork, T.2    Anoop, A.3    Thiel, W.4    Furstner, A.5
  • 35
    • 75749141777 scopus 로고    scopus 로고
    • For a recent review on (2 + 2) cycloadditions of allenes, see
    • For a recent review on (2 + 2) cycloadditions of allenes, see: B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Soc. Rev., 2010, 39, 783.
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 783
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3
  • 36
    • 77955799104 scopus 로고    scopus 로고
    • For a recent Au-catalyzed intermolecular (2 + 2) cycloaddition between alkynes and alkenes, see
    • For a recent Au-catalyzed intermolecular (2 + 2) cycloaddition between alkynes and alkenes, see: V. López-Carrillo and A. M. Echavarren, J. Am. Chem. Soc., 2010, 132, 9292-9294.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 9292-9294
    • López-Carrillo, V.1    Echavarren, A.M.2
  • 37
    • 79955604707 scopus 로고    scopus 로고
    • note
    • Additionally, in this reaction we also isolated a minor amount (17%) of the corresponding (2 + 2) adduct 4de.
  • 38
    • 79955603229 scopus 로고    scopus 로고
    • note
    • Submitting the (4 + 2) adduct 3dh to the reaction conditions provides 5dh, which confirms that 5dh is formed in situ from 3dh.
  • 39
    • 79955636020 scopus 로고    scopus 로고
    • note
    • Identification of isomeric adducts 3gi and 3gi' could be performed by NMR analysis. Moreover, the major isomer, 3gi, could be purified by crystallography, and further identified by X-ray diffraction
  • 40
    • 79955586719 scopus 로고    scopus 로고
    • note
    • The (2 + 2) adduct (4gi) was not detected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.