Lithium diisopropylamide-mediated enolizations: Solvent-independent rates, solvent-dependent mechanisms

Journal of the American Chemical Society

Volumn 122, Issue 11, 2000, Pages 2452-2458

  Sun, Xiufeng ^a   Collum, David B ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; HEMPA; LITHIUM DERIVATIVE; MONOMER; PYRIMIDINONE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; KINETICS; REACTION ANALYSIS; REACTION TIME; SOLVATION;

EID: 0034701307     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992062z     Document Type: Article

References (72)

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4. d'Angelo, J. Tetrahedron 1976, 32, 2979. Heathcock, C. H. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: New York, 1980; Vol. B, Chapter 4. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vols. 2 and 3. Snieckus, V. Chem. Rev. 1990, 90, 879.
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14. The relative rate constants were determined using 0.1 M LDA in neat ethereal solvents.
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27. Under these conditions, the enolate exists partially as a mixed dimer with LDA. Galiano-Roth, A. S.; Kim, Y.-J.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5053. Also, see ref 11.
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29. For leading references to detectable organolithium-substrate pre-complexation, see: Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1. For theoretical studies of substrate precomplexation, see: Bachrach, S. M.; Ritchie, J. P. J. Am. Chem. Soc. 1989, 111, 3134 and references therein. For a general discussion of ketone-lithium complexation and related ketone-Lewis acid complexation, see: Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 1, p 283.
30. For leading references to detectable organolithium-substrate pre- complexation, see: Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1. For theoretical studies of substrate precomplexation, see: Bachrach, S. M.; Ritchie, J. P. J. Am. Chem. Soc. 1989, 111, 3134 and references therein. For a general discussion of ketone-lithium complexation and related ketone-Lewis acid complexation, see: Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 1, p 283.
31. For leading references to detectable organolithium-substrate pre- complexation, see: Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1. For theoretical studies of substrate precomplexation, see: Bachrach, S. M.; Ritchie, J. P. J. Am. Chem. Soc. 1989, 111, 3134 and references therein. For a general discussion of ketone-lithium complexation and related ketone-Lewis acid complexation, see: Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 1, p 283.
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