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Volumn 61, Issue 25, 1996, Pages 8915-8920

Synthesis of novel chiral diazole derivative ligands for the enantioselective addition of diethylzinc to benzaldehyde

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EID: 0000015776     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961388c     Document Type: Article
Times cited : (64)

References (77)
  • 13
    • 85069128236 scopus 로고
    • Katritzky, A. R., Potts, K. T., Eds.; Pergamon Press: Oxford, Chapter 4.04.
    • Elguero, J. In Comprehensive Heterocydic Chemistry; Katritzky, A. R., Potts, K. T., Eds.; Pergamon Press: Oxford, 1984; Vol. 5, Chapter 4.04.
    • (1984) Comprehensive Heterocydic Chemistry , vol.5
    • Elguero, J.1
  • 14
    • 0003625968 scopus 로고
    • Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, Chapter 13.2.
    • Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1986; Vol. 2, Chapter 13.2.
    • (1986) Comprehensive Coordination Chemistry , vol.2
    • Reedijk, J.1
  • 29
    • 85082943077 scopus 로고
    • Epoxides are now readily available in optically pure form via chemical or biological transformations: Pfenninger, A. Synthesis 1986, 89.
    • (1986) Synthesis , pp. 89
    • Pfenninger, A.1
  • 34
    • 37049171559 scopus 로고
    • Commercially available optically active epoxides were used throughout this work, and all high-pressure reactions were conducted with a Hikari-Koatsu HR-15-B3 apparatus. Bis-epoxide 7 was prepared from D-mannitol according to the literature procedure: Wiggins, L. F. J. Chem. Soc. 1946, 384.
    • (1946) J. Chem. Soc. , pp. 384
    • Wiggins, L.F.1
  • 41
    • 85033536797 scopus 로고    scopus 로고
    • It has been known that 4 exists as a mixture of two tautomers in which the N2-H tautomer is the major component.6' All efforts to improve the regioselectivity in this reaction failed.
    • It has been known that 4 exists as a mixture of two tautomers in which the N2-H tautomer is the major component.6' All efforts to improve the regioselectivity in this reaction failed.
  • 45
    • 85033529252 scopus 로고    scopus 로고
    • The authors have deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinate can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
    • The authors have deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinate can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 46
    • 85033531128 scopus 로고    scopus 로고
    • It should be emphasized, however, that this argument is only based on solid-state conformational preferences, which may be quite different in solution.
    • It should be emphasized, however, that this argument is only based on solid-state conformational preferences, which may be quite different in solution.
  • 52
    • 85033535023 scopus 로고    scopus 로고
    • Wiley: New York, 1973; Collect.
    • Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 755.
    • Organic Syntheses , vol.5 , pp. 755
  • 74
    • 85033534245 scopus 로고    scopus 로고
    • PM3-optimized structures of the lowest energy conformations are shown. Calculations were performed by MOPAC '93 implemented in ANCHOR II, a molecular design system for SUN computers, developed by FUJITSU, Ltd., and Kureha Chemical Industry Co., Ltd., 1992. MOPAC 93: Stewart, J. J. P. Fujitsu, Ltd., Tokyo, Japan, 1993.
    • PM3-optimized structures of the lowest energy conformations are shown. Calculations were performed by MOPAC '93 implemented in ANCHOR II, a molecular design system for SUN computers, developed by FUJITSU, Ltd., and Kureha Chemical Industry Co., Ltd., 1992. MOPAC 93: Stewart, J. J. P. Fujitsu, Ltd., Tokyo, Japan, 1993.
  • 75
    • 0026738290 scopus 로고
    • Unless otherwise noted CDCb was used as the solvent for the NMR experiments.
    • For general experimental information, see our previous paper: Kotsuki, H.; Nishikawa, H.; Mon, Y.; Ochi, M. J. Org. Chem. 1992, 57, 5036. Unless otherwise noted CDCb was used as the solvent for the NMR experiments.
    • (1992) J. Org. Chem. , vol.57 , pp. 5036
    • Kotsuki, H.1    Nishikawa, H.2    Mon, Y.3    Ochi, M.4
  • 76
    • 85033539679 scopus 로고    scopus 로고
    • Unfortunately, the 13C NMR signals of the pentafluorophenyl ring were too weak to observe.
    • Unfortunately, the 13C NMR signals of the pentafluorophenyl ring were too weak to observe.
  • 77
    • 85033538665 scopus 로고    scopus 로고
    • Interestingly, the cyclohexane carbons were detected to be nonequivalent. Clearly, this may be indicative of an internal hydrogen bonding between hydroxyl and pyrazole nitrogen groups.
    • Interestingly, the cyclohexane carbons were detected to be nonequivalent. Clearly, this may be indicative of an internal hydrogen bonding between hydroxyl and pyrazole nitrogen groups.


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