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Volumn 48, Issue 46, 2009, Pages 8733-8735

Efficient chiral N-heterocyclic carbene/copper(I)-catalyzed asymmetric allylic arylation with aryl Grignard reagents

Author keywords

Allylic compounds; Asymmetric catalysis; Copper; Magnesium; N heterocyclic carbenes

Indexed keywords

ALLYLIC COMPOUNDS; ARYLATIONS; ASYMMETRIC CATALYSIS; COPPER CATALYST; ENANTIOMERIC EXCESS; GRIGNARD REAGENT; MONODENTATES; N-HETEROCYCLIC; N-HETEROCYCLIC CARBENES; REGIO-SELECTIVE;

EID: 70350599360     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904676     Document Type: Article
Times cited : (132)

References (33)
  • 2
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    • For recent reviews of Cu-catalyzed asymmetric allylic substitution: a) A. Kar, N. P. Argade, Synthesis 2005, 2995-3022;
    • (2005) Synthesis , pp. 2995-3022
    • Kar, A.1    Argade, N.P.2
  • 4
    • 22744436808 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4435-4439;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4435-4439
  • 16
    • 34250704681 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4554-4558.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4554-4558
  • 17
    • 34548183315 scopus 로고    scopus 로고
    • For iridium-catalyzed AAAr using arylzinc reagents with high ee values but lower regioselectivity: a) A. Alexakis, S. El Hajjaji, D. Polet, X. Rathgeb, Org. Lett. 2007, 9, 3393-3395;
    • (2007) Org. Lett. , vol.9 , pp. 3393-3395
    • Alexakis, A.1    El Hajjaji, S.2    Polet, D.3    Rathgeb, X.4
  • 26
    • 3042577485 scopus 로고    scopus 로고
    • see also reference [4c]: bidentate NHC and dialkylzincs
    • For copper-catalyzed asymmetric allylic alkylation using monodentate NHC and alkyl Grignard reagents; a) S. Tominaga, Y. Oi, T. Kato, D. K. An, S. Okamoto, Tetrahedron Lett. 2004, 45, 5585-5588; see also reference [4c]: bidentate NHC and dialkylzincs;
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5585-5588
    • Tominaga, S.1    Oi, Y.2    Kato, T.3    An, D.K.4    Okamoto, S.5
  • 29
    • 40149087402 scopus 로고    scopus 로고
    • For copper-catalyzed AAAr of vinylsilane substrates using bidentate NHC and diarylzincs, see ref. [5]
    • Y. Lee, K. Akiyama, D. G. Gillingham, M. K. Brown, A. H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 446-447. For copper-catalyzed AAAr of vinylsilane substrates using bidentate NHC and diarylzincs, see ref. [5].
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 446-447
    • Lee, Y.1    Akiyama, K.2    Gillingham, D.G.3    Brown, M.K.4    Hoveyda, A.H.5
  • 32
    • 70350607549 scopus 로고    scopus 로고
    • The current conditions were also applicable to a linear allylic bromide although the level of enantioselectivity was slightly lower than our previous report (reference [H]); the reaction of hex-2-enyl bromide with PhMgBr gave y product with 74% ee and a 91:9 γ/α ratio in 98% yield
    • The current conditions were also applicable to a linear allylic bromide although the level of enantioselectivity was slightly lower than our previous report (reference [H]); the reaction of hex-2-enyl bromide with PhMgBr gave y product with 74% ee and a 91:9 γ/α ratio in 98% yield.
  • 33
    • 70350607548 scopus 로고
    • U.S. Patent 5196607, March 23
    • G. J. Quallich, U.S. Patent 5196607, March 23,1993.
    • (1993)
    • Quallich, G.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.