메뉴 건너뛰기




Volumn 51, Issue 39, 2010, Pages 5134-5136

Organocatalytic asymmetric thio-Michael addition of arylmethyl mercaptans to cyclic enones by a primary amino acid

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; AMINO ACID; AMINOKETONE; DICHLOROMETHANE; KETONE DERIVATIVE; THIOL DERIVATIVE;

EID: 77956227289     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.089     Document Type: Article
Times cited : (20)

References (33)
  • 5
    • 57449121750 scopus 로고    scopus 로고
    • P.G.M. Wuts, T.W. Greene, 4th ed. Wiley-Interscience New Jersey
    • P.G.M. Wuts, T.W. Greene, Greene's Protective Groups in Organic Synthesis 4th ed. 2007 Wiley-Interscience New Jersey
    • (2007) Greene's Protective Groups in Organic Synthesis
  • 11
    • 62849091903 scopus 로고    scopus 로고
    • Asymmetric thio-Michael addition of benzyl mercaptan to acyclic enones or enals with an organic catalyst: Y. Liu, B. Sun, B. Wang, M. Wakem, and L. Deng J. Am. Chem. Soc. 131 2009 418
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 418
    • Liu, Y.1    Sun, B.2    Wang, B.3    Wakem, M.4    Deng, L.5
  • 17
    • 0037126839 scopus 로고    scopus 로고
    • Asymmetric thio-Michael addition of benzyl mercaptan to cyclic enones with an organic catalyst: P. McDaid, Y. Chen, and L. Deng Angew. Chem., Int. Ed. 41 2002 338
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 338
    • McDaid, P.1    Chen, Y.2    Deng, L.3
  • 29
    • 77956227579 scopus 로고    scopus 로고
    • note
    • TLC tracing of the reaction indicated that the thio-Michael addition using catalyst 1 proceeded cleanly to give the desired Michael adduct 3 and no major by-products were produced.
  • 30
    • 0037871675 scopus 로고    scopus 로고
    • DMSO will act as a weak Lewis base to dissolve an amino acid in the reaction media and to activate a mercaptan moderately. The use of a sulfoxide as a Lewis base was well studied by Kobayashi et al.: S. Kobayashi, C. Ogawa, H. Konishi, and M. Sugiura J. Am. Chem. Soc. 125 2003 6610
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6610
    • Kobayashi, S.1    Ogawa, C.2    Konishi, H.3    Sugiura, M.4
  • 31
    • 67549137639 scopus 로고    scopus 로고
    • For reviews on organocatalysis using a primary amines, see: L.-W. Xu, J. Luo, and Y. Lu Chem. Commun. 2009 1807
    • (2009) Chem. Commun. , pp. 1807
    • Xu, L.-W.1    Luo, J.2    Lu, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.