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Volumn 116, Issue 19, 1994, Pages 8837-8838

Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate O-Silyl Enolates: A Chiral Tridentate Chelate as a Ligand for Titanium(IV)

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EID: 0000376088     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00098a065     Document Type: Article
Times cited : (320)

References (25)
  • 13
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    • Morrison, J. D., Ed.; Asymmetric Synthesis; Academic Press: San Diego, CA, Chapter 2.
    • Heathcock, C. H. In The Aldol Addition Reaction; Morrison, J. D., Ed.; Asymmetric Synthesis; Academic Press: San Diego, CA, 1984; Vol. 3, Chapter 2.
    • (1984) The Aldol Addition Reaction , vol.3
    • Heathcock, C.H.1
  • 14
    • 33751385697 scopus 로고
    • Oguni and co-workers have described chiral Schiff base titanium alkoxide complexes which catalyze the enantioselective (62-97% ee) addition of TMSCN to aldehydes; see: See also: Nitta, H.; Yu, D.; Kudo, M.; Mori, A.; Inoue, S. J. Am. Chem. Soc. 1992, 114, 7969.
    • Oguni and co-workers have described chiral Schiff base titanium alkoxide complexes which catalyze the enantioselective (62-97% ee) addition of TMSCN to aldehydes; see: Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515. See also: Nitta, H.; Yu, D.; Kudo, M.; Mori, A.; Inoue, S. J. Am. Chem. Soc. 1992, 114, 7969.
    • (1993) J. Org. Chem. , vol.58 , pp. 1515
    • Hayashi, M.1    Miyamoto, Y.2    Inoue, T.3    Oguni, N.4
  • 17
    • 0001087427 scopus 로고
    • For a discussion of electronic tuning in asymmetric catalysis, see:
    • For a discussion of electronic tuning in asymmetric catalysis, see: Jacobsen, E. N.; Zhang, W.; Guler, M. L. J. Am. Chem. Soc. 1991, 113, 6703.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6703
    • Jacobsen, E.N.1    Zhang, W.2    Guler, M.L.3
  • 18
    • 1942447859 scopus 로고
    • For elegant studies on the mechanism of the asymmetric epoxidation, see:
    • For elegant studies on the mechanism of the asymmetric epoxidation, see: Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 113
    • Finn, M.G.1    Sharpless, K.B.2
  • 20
    • 33750368763 scopus 로고
    • Jacobsen has described the preparation of a large range of substituted salicylaldehydes; see:
    • Jacobsen has described the preparation of a large range of substituted salicylaldehydes; see: Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
    • (1994) J. Org. Chem. , vol.59 , pp. 1939
    • Larrow, J.F.1    Jacobsen, E.N.2    Gao, Y.3    Hong, Y.4    Nie, X.5    Zepp, C.M.6
  • 21
    • 0000389195 scopus 로고
    • Evaporation of toluene in vacuo has been reported to effect the removal of the i-PrOH liberated upon complex formation of Ti(0'Pr)4 with bidentate ligands such as a,a,a',a'-tetraaryl-l,3-dioxolane-4,5-dimethanols; see: and references therein.
    • Evaporation of toluene in vacuo has been reported to effect the removal of the i-PrOH liberated upon complex formation of Ti(0'Pr)4 with bidentate ligands such as a,a,a',a'-tetraaryl-l,3-dioxolane-4,5-dimethanols; see: Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171 and references therein.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 2171
    • Seebach, D.1    Plattner, D.A.2    Beck, A.K.3    Wang, Y.M.4    Hunziker, D.5    Petter, W.6
  • 24
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    • Jacobsen has utilized ligands prepared from di-tert-butyl-substituted salicylaldehydes in the preparation of enantioselective catalysts for asymmetric epoxidation; see:
    • Jacobsen has utilized ligands prepared from di-tert-butyl-substituted salicylaldehydes in the preparation of enantioselective catalysts for asymmetric epoxidation; see: Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7063
    • Jacobsen, E.N.1    Zhang, W.2    Muci, A.R.3    Ecker, J.R.4    Deng, L.5
  • 25
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    • Thus, increasing the strength of the RCHO-Ti interaction inevitably leads to an increase in the strength of the R'O-Ti bond. For strong M-O bonds the rate of silylation of the metal aldolate might be prohibitively slow, allowing a silicon-catalyzed process to compete effectively; see:
    • Thus, increasing the strength of the RCHO-Ti interaction inevitably leads to an increase in the strength of the R'O-Ti bond. For strong M-O bonds the rate of silylation of the metal aldolate might be prohibitively slow, allowing a silicon-catalyzed process to compete effectively; see: Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4323
    • Carreira, E.M.1    Singer, R.A.2


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