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Volumn 72, Issue 14, 2007, Pages 5270-5275

Cyclic oxonitriles: Stereodivergent Grignard addition-alkylations

Author keywords

[No Author keywords available]

Indexed keywords

GRIGNARD REAGENTS; NITRILES; STEREOCENTERS; STEREOELECTRONIC EFFECTS;

EID: 34447326159     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070678y     Document Type: Article
Times cited : (10)

References (49)
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    • For an excellent overview of terms, steric constraints, and orbital overlap see
    • For an excellent overview of terms, steric constraints, and orbital overlap see: Gawley, R. E. Tetrahedron Lett. 1999, 40, 4297.
    • (1999) Tetrahedron Lett , vol.40 , pp. 4297
    • Gawley, R.E.1
  • 31
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    • 8
    • 8
  • 32
    • 34447297704 scopus 로고    scopus 로고
    • Repetitive alkylations consistently proceed with the same yield, accompanied by the hydroxyalkenenitrile 12 (OMgMe = OH) resulting from carbonyl addition.
    • Repetitive alkylations consistently proceed with the same yield, accompanied by the hydroxyalkenenitrile 12 (OMgMe = OH) resulting from carbonyl addition.
  • 33
    • 34447294403 scopus 로고    scopus 로고
    • 12
    • 12
  • 34
    • 34447299001 scopus 로고    scopus 로고
    • -1: Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 696-697.
    • -1: Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 696-697.
  • 35
    • 0000526031 scopus 로고    scopus 로고
    • The fragmentation of β-alkoxynitriles is often facile and in this instance the formation of a dioxide likely facilitates the fragmentation to an even greater extent: (a) Carrier, P. R.; Lo, C. W.-S.; Lo, M. M.-C.; Wan, N. C.; Williams, I. D. Org. Lett. 2000, 2, 2443.
    • The fragmentation of β-alkoxynitriles is often facile and in this instance the formation of a dioxide likely facilitates the fragmentation to an even greater extent: (a) Carrier, P. R.; Lo, C. W.-S.; Lo, M. M.-C.; Wan, N. C.; Williams, I. D. Org. Lett. 2000, 2, 2443.
  • 37
    • 34447306446 scopus 로고    scopus 로고
    • X-ray crystallography of 14b, and derivatives of 14a, 14c, and 14d, confirmed the stereochemical assignments. The authors have deposited the crystallographic data with the Cambridge Crystallographic Data Center. The data can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
    • X-ray crystallography of 14b, and derivatives of 14a, 14c, and 14d, confirmed the stereochemical assignments. The authors have deposited the crystallographic data with the Cambridge Crystallographic Data Center. The data can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 39
    • 34447332675 scopus 로고    scopus 로고
    • Considerable amounts of starting oxonitrile 1c, the hydroxyalkenenitrile i, and the hydroxyalkanenitrile ii are generated, which result from incomplete conjugate addition and alkylation, respectively. (Chemical Equation Presented)
    • Considerable amounts of starting oxonitrile 1c, the hydroxyalkenenitrile i, and the hydroxyalkanenitrile ii are generated, which result from incomplete conjugate addition and alkylation, respectively. (Chemical Equation Presented)
  • 40
    • 34447312742 scopus 로고    scopus 로고
    • 9
    • 9
  • 43
    • 34447302962 scopus 로고    scopus 로고
    • 1H NMR analysis of the crude reaction mixture failed to identify any enamide.
    • 1H NMR analysis of the crude reaction mixture failed to identify any enamide.
  • 47
    • 0034639903 scopus 로고    scopus 로고
    • N2′ alkylation: Alnajjar, M. S.; Smith, G. F.; Kuivila, H. G. J. Org. Chem. 1984, 49, 1271.
    • N2′ alkylation: Alnajjar, M. S.; Smith, G. F.; Kuivila, H. G. J. Org. Chem. 1984, 49, 1271.
  • 48
    • 34447339274 scopus 로고    scopus 로고
    • Presumably the ejection of bromide is faster than reorganization to a C-magnesiated nitrile followed by loss of bromide.
    • Presumably the ejection of bromide is faster than reorganization to a C-magnesiated nitrile followed by loss of bromide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.