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Volumn 692, Issue 1-3, 2007, Pages 579-584

Copper-catalyzed transformation of carbonyl-ene-nitrile compounds: Vinylation, imino ene reaction, and alkynylation of 2-aza-2,4-cyclopentadienone intermediates generated via Ritter-type hydration and dehydrative cyclization reactions

Author keywords

Allylation; Azacyclopentadienone; Carbonyl ene nitrile; Copper(II) catalysis; Pyrrolinone; Vinylation

Indexed keywords

CATALYSIS; COPPER COMPOUNDS; HYDRATION; KETONES; OLEFINS; REACTION KINETICS;

EID: 33845625717     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.04.053     Document Type: Article
Times cited : (12)

References (66)
  • 3
    • 26844464677 scopus 로고    scopus 로고
    • For recent reviews, see:
    • For recent reviews, see:. Miki K., Uemura S., and Ohe K. Chem. Lett. 34 (2005) 1068
    • (2005) Chem. Lett. , vol.34 , pp. 1068
    • Miki, K.1    Uemura, S.2    Ohe, K.3
  • 34
    • 27144534048 scopus 로고    scopus 로고
    • Ni- and Fe-catalyzed tandem cyanation and cyclization of α-ketoalkynes to afford pyrrolinone derivatives have been reported, see:
    • Ni- and Fe-catalyzed tandem cyanation and cyclization of α-ketoalkynes to afford pyrrolinone derivatives have been reported, see:. Rosas N., Sharma P., Arellano I., Ramírez M., Pérez D., Hernández S., and Cabrera A. Organometallics 24 (2005) 4893
    • (2005) Organometallics , vol.24 , pp. 4893
    • Rosas, N.1    Sharma, P.2    Arellano, I.3    Ramírez, M.4    Pérez, D.5    Hernández, S.6    Cabrera, A.7
  • 36
    • 0346360375 scopus 로고    scopus 로고
    • The catalytic furan formation from the same carbonyl-ene-nitrile compounds using acylpalladium species has been reported, see:
    • The catalytic furan formation from the same carbonyl-ene-nitrile compounds using acylpalladium species has been reported, see:. Nozaki K., Sato N., and Takaya H. Bull. Chem. Soc. Jpn. 69 (1996) 1629
    • (1996) Bull. Chem. Soc. Jpn. , vol.69 , pp. 1629
    • Nozaki, K.1    Sato, N.2    Takaya, H.3
  • 37
    • 33845641016 scopus 로고    scopus 로고
    • note
    • To avoid a polymerization of 4-methoxystyrene under protic conditions, we attempted the reaction of 1 with 4-methoxystyrene without water, but the desired product was not obtained at all.
  • 40
    • 33845652687 scopus 로고    scopus 로고
    • note
    • Cationic species is a most likely intermediate.
  • 41
    • 0001096447 scopus 로고
    • High-pressure-promoted [2 + 2] cycloadditions of imines gave vinylated products as minor products, see:
    • High-pressure-promoted [2 + 2] cycloadditions of imines gave vinylated products as minor products, see:. Aben R.W.M., Smit R., and Scheeren J.W. J. Org. Chem. 52 (1987) 365
    • (1987) J. Org. Chem. , vol.52 , pp. 365
    • Aben, R.W.M.1    Smit, R.2    Scheeren, J.W.3
  • 42
    • 0141786838 scopus 로고    scopus 로고
    • For transition metal-mediated allylamine formations from imines and vinylmetals, see:
    • For transition metal-mediated allylamine formations from imines and vinylmetals, see:. Fukuhara K., Okamoto S., and Sato F. Org. Lett. 5 (2003) 2145
    • (2003) Org. Lett. , vol.5 , pp. 2145
    • Fukuhara, K.1    Okamoto, S.2    Sato, F.3
  • 44
    • 15044342248 scopus 로고    scopus 로고
    • For recent examples of Morita-Baylis-Hillman Reaction of imines leading to allylamines, see:
    • For recent examples of Morita-Baylis-Hillman Reaction of imines leading to allylamines, see:. Shi M., Xu Y.-M., and Shi Y.-L. Chem. Eur. J. 11 (2005) 1794
    • (2005) Chem. Eur. J. , vol.11 , pp. 1794
    • Shi, M.1    Xu, Y.-M.2    Shi, Y.-L.3
  • 48
    • 0033601460 scopus 로고    scopus 로고
    • Transition metal-catalyzed alkenylation of imines to give allylamines has been well investigated. For selected examples, see:
    • Transition metal-catalyzed alkenylation of imines to give allylamines has been well investigated. For selected examples, see:. Oi S., Moro M., Fukuhara H., Kawanishi T., and Inoue Y. Tetrahedron Lett. 40 (1999) 9259
    • (1999) Tetrahedron Lett. , vol.40 , pp. 9259
    • Oi, S.1    Moro, M.2    Fukuhara, H.3    Kawanishi, T.4    Inoue, Y.5
  • 50
    • 0032541549 scopus 로고    scopus 로고
    • Addition reactions of organometallic reagents to imines are well-known methods for synthesis of allylamines, see also:
    • Addition reactions of organometallic reagents to imines are well-known methods for synthesis of allylamines, see also:. Andersson P.G., Johansson F., and Tanner D. Tetrahedron 54 (1998) 11549
    • (1998) Tetrahedron , vol.54 , pp. 11549
    • Andersson, P.G.1    Johansson, F.2    Tanner, D.3
  • 52
    • 0028952646 scopus 로고
    • Transiton metal-catalyzed imino ene reactions have been intensively studied, see:
    • Transiton metal-catalyzed imino ene reactions have been intensively studied, see:. Borzilleri R.M., and Weinreb S.M. Synthesis (1995) 347
    • (1995) Synthesis , pp. 347
    • Borzilleri, R.M.1    Weinreb, S.M.2
  • 55
    • 33845666654 scopus 로고    scopus 로고
    • note
    • w = 0.0853, Goodness-of-fit = 1.039.
  • 56
    • 0033537047 scopus 로고    scopus 로고
    • Alkynylation of imines with terminal alkynes has been reported, see:
    • Alkynylation of imines with terminal alkynes has been reported, see:. Frantz D.E., Fassler R., and Carreira E.M. J. Am. Chem. Soc. 121 (1999) 11245
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11245
    • Frantz, D.E.1    Fassler, R.2    Carreira, E.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.