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Volumn 64, Issue 20, 1999, Pages 7537-7546

Carboindation of carbon - Carbon triple bonds: Regioselective indium- mediated allylation of functionalized alkynes and transformation into halogen-substituted 1,4-dienes

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYNE; INDIUM;

EID: 0033214815     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9908593     Document Type: Article
Times cited : (66)

References (50)
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  • 16
    • 84990107570 scopus 로고
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38. (c) Knochel, P. Carbometalation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911.
    • (1989) Angew, Chem., Int. Ed. Engl. , vol.28 , pp. 38
    • Oppolzer, W.1
  • 17
    • 0001522634 scopus 로고
    • Carbometalation of Alkenes and Alkynes
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
    • For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38. (c) Knochel, P. Carbometalation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 865-911
    • Knochel, P.1
  • 22
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    • After this paper was submitted, an addional report was published: (b) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
    • (1999) J. Org. Chem. , vol.64 , pp. 4095
    • Fujiwara, N.1    Yamamoto, Y.2
  • 24
    • 0344338341 scopus 로고    scopus 로고
    • note
    • We interpret the beneficial yields to arise from a loss of chelation upon the addition of TMSCl, which destabilizes the vinylic indium intermediate and thereby facilitates the subsequent aqueous workup. No In-Si interchange was observed.
  • 26
    • 0345632804 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy).
  • 27
    • 0344338338 scopus 로고    scopus 로고
    • note
    • The observation of probable radical pathways in carboindation reactions has been described; see ref 9.
  • 28
    • 0344770339 scopus 로고    scopus 로고
    • note
    • The double substitution of carboindation products might proceed by a fast consecutive exchange, possibly via intermediacy of a sterically less crowded haloindium carbenoid.
  • 30
    • 0344338337 scopus 로고    scopus 로고
    • note
    • Linear 1,4-dienes were found to have the E configuration, as a result of syn addition of the organoindium reagent. No Z-dienes were detected; see ref 9.
  • 31
    • 0345632800 scopus 로고    scopus 로고
    • note
    • The origin of the differences for 17a and 17b might arise from enhanced steric crowding in the bicyclic chelated transition state for 17b relative to that for 17a. Alternatively, chelation in the bicyclic transition state for 17b might be destabilized relative to that for 17a due to the presence of the electron-withdrawing ester group in 17b.
  • 32
    • 0001015055 scopus 로고    scopus 로고
    • Therefore, the carboxylic acid moiety is not as strongly chelating as the hydroxyl moiety in this case, which contrasts the findings in carbonyl addition reactions; see: Bernardelli, P.; Paquette, L. A. J. Org. Chem. 1997, 62, 8284.
    • (1997) J. Org. Chem. , vol.62 , pp. 8284
    • Bernardelli, P.1    Paquette, L.A.2
  • 33
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    • note
    • In carbonyl addition reactions only two of three ligands typically react; see ref 11.
  • 35
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    • note
    • A possible fast intramolecular proton transfer (via a six-membered ring) from the hydroxy group to the In-centered carbon would result in "quenching" of the In atom in syn orientation to the hydroxy group.
  • 39
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    • 1a: Kwart, H.; Sarner, S. F.; Slutsky, J. J. Am. Chem. Soc. 1973, 95, 5234. 1c: Logue, M. W.; Teng, K. J. Org. Chem. 1982, 47, 2549.
    • (1982) J. Org. Chem. , vol.47 , pp. 2549
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  • 49
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    • Itoh, K.; Nishiyama, H. Heterocycles 1984, 21, 449. For the corresponding E-isomer, see: Ishino, Y.; Wakamoto, K.; Hirashima, T. Chem. Lett. 1984, 765.
    • (1984) Heterocycles , vol.21 , pp. 449
    • Itoh, K.1    Nishiyama, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.