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Volumn 8, Issue 21, 2006, Pages 4903-4906

Oxonitriles: A Grignard addition-acylation route to enamides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NITRILE;

EID: 33750337500     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0619765     Document Type: Article
Times cited : (13)

References (42)
  • 2
    • 33750379684 scopus 로고    scopus 로고
    • Ref 1
    • For Robinson annulations with β-oxonitriles, see: (a) Ref 1.
  • 29
    • 33750370704 scopus 로고    scopus 로고
    • Ref 10f
    • Attempts to detect the intermediate acyl ketenimine have not been successful, consistent with their known instability: (a) Ref 10f.
  • 34
    • 33750297998 scopus 로고    scopus 로고
    • note
    • Attempts to intercept 2 with acryloyl chloride were not successful.
  • 35
    • 33750346065 scopus 로고    scopus 로고
    • note
    • The N-acylation of 2 with pivaloyl chloride implies that methyl chloroformate acylates first on nitrogen and then on oxygen as shown (Scheme 2).
  • 36
    • 33750322119 scopus 로고    scopus 로고
    • note
    • 4), concentrated, and purified by radial chromatography to afford the pure enamide.
  • 37
    • 33750312049 scopus 로고    scopus 로고
    • or from the 12 Union Road, Cambridge CB2 1EZ, U.K. (fax +44 1223 336033; or deposit@ccdc.cam.ac.uk.)
    • X-ray crystallography of 8b and 8g confirmed the stereochemical assignment. The authors have deposited the crystallographic data for 8b and 8g with the Cambridge Crystallographic Data Center (CCDC 605398 and 605397, respectively). The supplementary crystallographic data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, U.K. (fax +44 1223 336033; or deposit@ccdc.cam.ac.uk.).
  • 39
    • 33750344533 scopus 로고    scopus 로고
    • note
    • The unit cell contains three distinct conformers: the conformer shown in Figure 1, a second similar conformer in which the phenyl group is axial, and a third conformer with a ring-flipped cyclohexane ring in which the phenyl substituent is equatorially oriented. An ORTEP diagram is provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.