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Volumn 53, Issue 6, 2014, Pages 1611-1615

Chemoselective catalytic conjugate addition of alcohols over amines

Author keywords

amino alcohols; chemoselective catalysis; cooperative effects; proton transfer; synthetic methods

Indexed keywords

CHEMOSELECTIVE; CO-OPERATIVE EFFECTS; CONJUGATE ADDITION; COPPER CATALYST; HYDROXY GROUPS; PROTECTING GROUP; SYNTHETIC METHODS; UNSATURATED NITRILES;

EID: 84893457509     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309755     Document Type: Article
Times cited : (45)

References (46)
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    • Recently reported catalyst-controlled C-O versus C-N allylic functionalization:, I. I. Strambeanu, M. C. White, J. Am. Chem. Soc. 2013, 135, 12032.
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  • 39
    • 34248573312 scopus 로고    scopus 로고
    • Aniline shows a comparable nucleophilicity to primary alkyl amines, see:, F. Brotzel, Y. C. Chu, H. Mayr, J. Org. Chem. 2007, 72, 3679.
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    • Brotzel, F.1    Chu, Y.C.2    Mayr, H.3
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    • 79955419410 scopus 로고    scopus 로고
    • For the utility of tetrazole as a carboxylic acid bioisostere, see
    • For the utility of tetrazole as a carboxylic acid bioisostere, see:, N. A. Meanwell, J. Med. Chem. 2011, 54, 2529.
    • (2011) J. Med. Chem. , vol.54 , pp. 2529
    • Meanwell, N.A.1
  • 44
    • 0036589307 scopus 로고    scopus 로고
    • It is unclear whether simultaneous activation of acrylonitrile and alcohol is operative because intramolecular conjugate addition of copper(I) alkoxide coordinated by acrylonitrile in an end-on fashion would be sterically unlikely. Coordination in an end-on fashion for nitrile functionality, see:, V. Y. Kukushkin, A. J. L. Pombeiro, Chem. Rev. 2002, 102, 1771. For further discussion, see Supporting Information.
    • (2002) Chem. Rev. , vol.102 , pp. 1771
    • Kukushkin, V.Y.1    Pombeiro, A.J.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.