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Volumn 113, Issue 25, 1991, Pages 9571-9574

Effects of Lithium Salts on the Stereochemistry of Ketone Enolization by Lithium 2,2,6,6-Tetramethylpiperidide (LiTMP). A Convenient Method for Highly E-Selective Enolate Formation

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EID: 0000094425     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00025a023     Document Type: Article
Times cited : (158)

References (59)
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    • Morrison, J. D., Ed.; Academic Press: New York Chapter 1.
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    • (1983) Asymmetric Synthesis , pp. 3
    • Evans, D.A.1
  • 5
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    • For other examples of the use of lithium amide/R3SiCl mixtures, see
    • For other examples of the use of lithium amide/R3SiCl mixtures, see: Taylor, S. L.; Lee, D. Y.; Martin, J. C. J. Org. Chem. 1983, 48, 4156.
    • (1983) J. Org. Chem. , vol.48 , pp. 4156
    • Taylor, S.L.1    Lee, D.Y.2    Martin, J.C.3
  • 22
    • 0024816607 scopus 로고
    • Less direct, yet highly selective syntheses of lithium enolates
    • Less direct, yet highly selective syntheses of lithium enolates: Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedron Lett. 1989, 30, 7121.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7121
    • Paterson, I.1    Goodman, J.M.2    Isaka, M.3
  • 27
    • 0001947228 scopus 로고
    • Other studies of E/Z enolization selectivity
    • Other studies of E/Z enolization selectivity: Prieto, J. A.; Suarez, J.; Larson, G. L. Synth. Commun. 1988, 18, 253.
    • (1988) Synth. Commun. , vol.18 , pp. 253
    • Prieto, J.A.1    Suarez, J.2    Larson, G.L.3
  • 42
    • 0013487871 scopus 로고
    • In recent studies of ketone enolization, Saunders concluded that the reaction is under exclusively kinetic control.
    • In recent studies of ketone enolization, Saunders concluded that the reaction is under exclusively kinetic control. Xie, L.; Saunders, W. H., Jr. J. Am. Chem. Soc. 1991, 113, 3123.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 3123
    • Xie, L.1    Saunders, W.H.2
  • 52
    • 33845281229 scopus 로고
    • Snaith and co-workers clearly articulated the merits of NH4X salts as precursors to anhydrous LiX salts
    • Snaith and co-workers clearly articulated the merits of NH4X salts as precursors to anhydrous LiX salts: Barr, D.; Snaith, R.; Wright, D. S.; Mulvey, R. E.; Wade, K. J. Am. Chem. Soc. 1987, 109, 7891.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7891
    • Barr, D.1    Snaith, R.2    Wright, D.S.3    Mulvey, R.E.4    Wade, K.5
  • 53
    • 33751499786 scopus 로고
    • Ireland recently concluded that lithium amide-mediated ester enolate formation is under kinetic control
    • Ireland recently concluded that lithium amide-mediated ester enolate formation is under kinetic control: Ireland, R. E.; Wipf, P.; Armstrong, J. D., III J. Org. Chem. 1991, 56, 650.
    • (1991) J. Org. Chem. , vol.56 , pp. 650
    • Ireland, R.E.1    Wipf, P.2    Armstrong, J.D.3
  • 55
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    • Pray, A. R. Inorg. Synth. 1957, 5, 153. Simmons, J. P.; Freimuth, H.; Russell, H. J. Am. Chem. Soc. 1936, 58, 1692.
    • (1957) Inorg. Synth. , vol.5 , pp. 153
    • Pray, A.R.1
  • 59
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    • The requisite 2-methyl-2-nitropropane is commercially available or made by a literature method; Wiley: New York, Collect.
    • The requisite 2-methyl-2-nitropropane is commercially available or made by a literature method; Calder, A.; Forrester, A. R.; Hepburn, S. P. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 803.
    • (1988) Organic Syntheses , vol.VI , pp. 803
    • Calder, A.1    Forrester, A.R.2    Hepburn, S.P.3


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