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Volumn 45, Issue 29, 2004, Pages 5585-5588

γ-Selective allylic substitution reaction with Grignard reagents catalyzed by copper N-heterocyclic carbene complexes and its application to enantioselective synthesis

Author keywords

Allylic substitution; Asymmetric reaction; N Heterocyclic carbene; Organocopper

Indexed keywords

CARBENOID; COPPER DERIVATIVE; N HETEROCYCLIC CARBENE; UNCLASSIFIED DRUG;

EID: 3042577485     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.135     Document Type: Article
Times cited : (111)

References (28)
  • 2
    • 0004228992 scopus 로고
    • For organocopper chemistry, see: R.J.K. Taylor. Oxford: Oxford University Press
    • For organocopper chemistry, see: Taylor R.J.K. Organocopper Reagents. 1994;Oxford University Press, Oxford
    • (1994) Organocopper Reagents
  • 15
    • 0035968410 scopus 로고    scopus 로고
    • Asymmetric conjugate addition reactions catalyzed by copper imidazolium carbene complexes:
    • Asymmetric conjugate addition reactions catalyzed by copper imidazolium carbene complexes: Guillen F., Winn C.L., Alexakis A. Tetrahedron: Asymmetry. 12:2001;2083
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2083
    • Guillen, F.1    Winn, C.L.2    Alexakis, A.3
  • 18
    • 0141631426 scopus 로고    scopus 로고
    • Other catalyses with copper imidazolium carbene complexes in organic synthesis:
    • Other catalyses with copper imidazolium carbene complexes in organic synthesis: Jurkauskas V., Sadighi J.P., Buchwald S.L. Org. Lett. 5:2003;2417
    • (2003) Org. Lett. , vol.5 , pp. 2417
    • Jurkauskas, V.1    Sadighi, J.P.2    Buchwald, S.L.3
  • 19
    • 1542647135 scopus 로고    scopus 로고
    • and references for recent structural studies of N-heterocyclic carbene copper complexes cited therein
    • Kaur H., Zinn F.K., Stevens E.D., Nolan S.P. Organometallics. 23:2004;1157. and references for recent structural studies of N-heterocyclic carbene copper complexes cited therein
    • (2004) Organometallics , vol.23 , pp. 1157
    • Kaur, H.1    Zinn, F.K.2    Stevens, E.D.3    Nolan, S.P.4
  • 20
    • 3042549319 scopus 로고    scopus 로고
    • note
    • 2OClCu: C, 60.79; H, 5.37; N, 7.46. Found: C, 60.95; H, 5.54; N, 7.47
  • 21
    • 3042553303 scopus 로고    scopus 로고
    • note
    • 4Cl was added. Usual extractive work-up and passing through a short silica gel column yielded a mixture of α- and γ-products
  • 22
    • 3042547223 scopus 로고    scopus 로고
    • note
    • TLC analysis of the reaction mixture indicated that for complete consumption of 1a it needed 2 h for the reaction with 4a and 30 min for the reaction with 4b
  • 23
    • 1842429742 scopus 로고    scopus 로고
    • Synthesis and structural study of (NHC)Cu(I) methyl complex were reported:
    • Synthesis and structural study of (NHC)Cu(I) methyl complex were reported: Mankad N.P., Gray T.G., Laitar D.S., Sadighi J.P. Organometallics. 23:2004;1191
    • (2004) Organometallics , vol.23 , pp. 1191
    • Mankad, N.P.1    Gray, T.G.2    Laitar, D.S.3    Sadighi, J.P.4
  • 24
    • 3042549318 scopus 로고    scopus 로고
    • note
    • 4c t-BuONa and CuCl in THF. The resulting mixture was filtered through a pad of Celite and the filtrate was stored under Ar. The THF-solution containing 4c-f, respectively, thus obtained was charged into the reaction vessel and THF was removed under reduced pressure prior to use
  • 25
    • 3042695123 scopus 로고    scopus 로고
    • note
    • 34OSi: C, 71.04; H, 12.67. Found: C, 70.64; H, 13.00
  • 28
    • 3042695124 scopus 로고    scopus 로고
    • note
    • N2′ fashion (unpublished results)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.