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Volumn 76, Issue 6, 2011, Pages 1814-1820

Asymmetric synthesis of ethoxydienamines in superbasic medium mediated by chiral sulfinyl group

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; CHIRAL AUXILIARIES; DIASTEREO-SELECTIVITY; ELIMINATION REACTION; ENANTIOPURE; FUNCTIONALIZED; SELECTIVE REMOVAL; SULFINIMINES; SULFINYL GROUP;

EID: 79953841874     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1024943     Document Type: Article
Times cited : (4)

References (35)
  • 1
    • 33751559719 scopus 로고    scopus 로고
    • Davis, F. A. J. Org. Chem. 2006, 71 (24), 8993-9003.
    • (2006) J. Org. Chem. , vol.71 , Issue.24 , pp. 8993-9003
    • Davis, F.A.1
  • 21
    • 34250824031 scopus 로고    scopus 로고
    • Davis, F. A.; M., S. Org. Lett. 2007, 9 (12), 2413-2416.
    • (2007) Org. Lett. , vol.9 , Issue.12 , pp. 2413-2416
    • Davis, F.A.M.S.1
  • 33
    • 79953844724 scopus 로고    scopus 로고
    • note
    • Thioester C has been recovered in 42% yield under these reaction conditions. An alternative explanation could be the attack of the nucleophile at sulfur; to this purpose we tried tert-butansulfinylimine (E)-N-benzylidene-2- methylpropane-2-sulfinamide under the same reaction conditions but the yield remained low.
  • 34
    • 79953854144 scopus 로고    scopus 로고
    • note
    • Enantiomeric purity has been verified using Eu(hfc)3 as chiral shift reagent.
  • 35
    • 79953863069 scopus 로고    scopus 로고
    • note
    • HCl, TFA, triflic acid, and chloromethanesulfonic acid were used as acidic catalysts under various conditions, but in every case the unreacted alkoxydienylamine 5 was recovered.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.