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Volumn 45, Issue 24, 2006, Pages 4019-4023

A general and versatile method for C-C cross-coupling synthesis of conjugated enynes: One-pot sequence starting from carbonyl compounds

Author keywords

C C coupling; Cross coupling; Enynes; Homogeneous catalysis; Phosphazene bases

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; CHEMICAL BONDS; KETONES; SYNTHESIS (CHEMICAL);

EID: 33746315997     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504594     Document Type: Article
Times cited : (28)

References (40)
  • 1
    • 33746302238 scopus 로고
    • The chemistry of carbonyl compounds is virtually the backbone of synthetic organic chemistry
    • Benjamin, New York
    • "The chemistry of carbonyl compounds is virtually the backbone of synthetic organic chemistry": J. D. Roberts, M. C. Caserio, Basic Principles of Organic Chemistry, Benjamin, New York, 1965, p. 426.
    • (1965) Basic Principles of Organic Chemistry , pp. 426
    • Roberts, J.D.1    Caserio, M.C.2
  • 7
    • 0344132082 scopus 로고    scopus 로고
    • b) S. Bräse, Synlett 1999, 1654-1656.
    • (1999) Synlett , pp. 1654-1656
    • Bräse, S.1
  • 18
    • 33746283365 scopus 로고    scopus 로고
    • note
    • Trialkylamines are not basic enough to promote the nonaflation, whereas DBU gives low conversions as a result of the side reaction with NfF. The results will be reported in a subsequent full account.
  • 26
    • 33746301078 scopus 로고    scopus 로고
    • note
    • Preliminary investigations show that the nonaflation/elimination protocol is applicable to a wide range of carbonyl compounds, leading to terminal or internal alkynes or allenes, depending on the stereoelectronic effects of the substituents in the carbonyl substrate. The results will be reported in due course.
  • 27
    • 33746310030 scopus 로고    scopus 로고
    • note
    • 2 base (1 equiv) and NfF under the kinetic conditions, we could detect only mixtures of the alkyne and the starting material, which clearly indicates that nonaflation is the rate-determining step.
  • 28
    • 33746305592 scopus 로고    scopus 로고
    • note
    • 3Si, under our reaction conditions.
  • 29
    • 33746284549 scopus 로고    scopus 로고
    • note
    • 2NEt in MeCN at -45°C to 5°C. The pure Z isomer was then isolated by preparative HPLC (68% yield).
  • 31
    • 85047671181 scopus 로고
    • The antimycotic agent terbinafine (Lamisil) manufactured by Novartis Pharmaceuticals is perhaps most prominent example of a widely applied drug bearing an eneyne structural motif; for other interesting bioactive compounds, see: a) L. Garlaschelli, E. Magistrali, G. Vidari, O. Zuffardi, Tetrahedron Lett. 1995, 36, 5633-5636;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5633-5636
    • Garlaschelli, L.1    Magistrali, E.2    Vidari, G.3    Zuffardi, O.4
  • 34


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.