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Volumn 7, Issue 18, 2001, Pages 4035-4046

A one-pot sequence of Stille and Heck couplings: Synthesis of various 1,3,5-hexatrienes and their subsequent 6π-electrocyclizations

Author keywords

Bicyclic systems; Chemoselectivity; Cross coupling; Electrocyclic addition; Palladium

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; ORGANIC COMPOUNDS; PALLADIUM;

EID: 0035903689     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010917)7:18<4035::AID-CHEM4035>3.0.CO;2-P     Document Type: Article
Times cited : (64)

References (70)
  • 16
    • 0000633011 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford
    • d) R. F. Heck in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1979, pp. 833-865;
    • (1979) Comprehensive Organic Synthesis , vol.4 , pp. 833-865
    • Heck, R.F.1
  • 17
  • 25
    • 0000725544 scopus 로고    scopus 로고
    • (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim
    • For reviews on this reaction see: a) T. N. Mitchell in Metal Catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 167-202;
    • (1998) Metal Catalyzed Cross-coupling Reactions , pp. 167-202
    • Mitchell, T.N.1
  • 27
    • 0000430830 scopus 로고
    • (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford
    • c) V. Farina in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, p. 200;
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 200
    • Farina, V.1
  • 32
    • 0025880698 scopus 로고
    • The reverse sequence of a palladium-catalyzed Heck-type coupling followed by an intramolecular Stille coupling has previously been reported, see: a) J. M. Nuss, B. H. Levine, R. A. Rennels, M. M. Heravi, Tetrahedron Lett. 1991, 32, 5243-5246;
    • (1991) Tetrahedron Lett. , vol.32 , pp. 5243-5246
    • Nuss, J.M.1    Levine, B.H.2    Rennels, R.A.3    Heravi, M.M.4
  • 47
    • 0000945478 scopus 로고
    • 2,4,6-Triisopropylbenzenesulfonylhydrazones are less prone than tosylhydrazones to undergo side reactions upon treatment with butyllithium, see: A. R. Chamberlin, J. E. Stemke, F. T. Bond, J. Org. Chem. 1978, 43, 147-154.
    • (1978) J. Org. Chem. , vol.43 , pp. 147-154
    • Chamberlin, A.R.1    Stemke, J.E.2    Bond, F.T.3
  • 48
    • 0001026714 scopus 로고
    • Treatment of cyclohexanonetosylhydrazone with 4 equiv nBuLi and then trimethyltin chloride has been reported to give the trimethyltin analogue of 23 in 47% yield, see: R. T. Taylor, C. R. Degenhardt, W. P. Melega, L. A. Paquette, Tetrahedron Lett. 1977, 18, 159-162.
    • (1977) Tetrahedron Lett. , vol.18 , pp. 159-162
    • Taylor, R.T.1    Degenhardt, C.R.2    Melega, W.P.3    Paquette, L.A.4
  • 62
    • 0003471284 scopus 로고    scopus 로고
    • unpublished results
    • Cyclopropyl ethenyl ketone was prepared from 1-cyclopropylcyclopropanol (ref. [30]) adopting a protocol of Kulinkovich et al. (ref. [31]). A. de Meijere, V. V. Bagutskii, O. G. Kulinkovich, unpublished results.
    • De Meijere, A.1    Bagutskii, V.V.2    Kulinkovich, O.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.