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Volumn 47, Issue 22, 2008, Pages 4196-4199

Catalytic enantioselective aldol-type reaction of β-ketosters with acetals

Author keywords

ketoester; Acetal; Aldol reaction; Palladium; Platinum

Indexed keywords

ACIDS; CHEMICAL REACTIONS; DYES; ENANTIOSELECTIVITY; ESTERS; PALLADIUM; PLATINUM; PLATINUM COMPOUNDS;

EID: 53549115640     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705344     Document Type: Article
Times cited : (55)

References (46)
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    • Recently, nonasymmetric hydroxymethylation of β-ketoesters with formalin catalyzed by an iron salt was reported: C. Ogawa, S. Kobayashi, Chem. Lett. 2007, 36, 56-57.
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    • Acetals were prepared according to the following reports. Ethyl acetal: a J. A. Vanallan, Org. Synth. Collect. IV 1963, 21-22;
    • Acetals were prepared according to the following reports. Ethyl acetal: a) J. A. Vanallan, Org. Synth. Collect. Vol. IV 1963, 21-22;
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    • We recently found that ethanol was oxidized in the presence of 1a to give a Pd-H species, which underwent asymmetric conjugate reduction of enones. See, Y. Tsuchiya, Y. Hamashima, M. Sodeoka, Org. Lett. 2006, 8, 4851-4854
    • We recently found that ethanol was oxidized in the presence of 1a to give a Pd-H species, which underwent asymmetric conjugate reduction of enones. See, Y. Tsuchiya, Y. Hamashima, M. Sodeoka, Org. Lett. 2006, 8, 4851-4854.
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    • We recently reported that the Pt-binap complex gave better results in the addition reaction of β-ketoesters to paraformaldehyde. See, reference [6
    • We recently reported that the Pt-binap complex gave better results in the addition reaction of β-ketoesters to paraformaldehyde. See, reference [6].
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    • 2 gave poor results (11% yield and 0% ee after 45 h, 0% yield after 24 h, respectively).
    • 2 gave poor results (11% yield and 0% ee after 45 h, 0% yield after 24 h, respectively).
  • 45
    • 53549084411 scopus 로고    scopus 로고
    • CCDC-66 2229 (4aa) and CCDC-677026 (4 cd) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. In the case of 4cd, X-ray analysis was carried out after the conversion to the corresponding camphor derivative. Details of the conversion and the crystallographic studies are described in the Supporting Information.
    • CCDC-66 2229 (4aa) and CCDC-677026 (4 cd) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. In the case of 4cd, X-ray analysis was carried out after the conversion to the corresponding camphor derivative. Details of the conversion and the crystallographic studies are described in the Supporting Information.
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    • A similar methyl acetal was formed when a catalytic asymmetric Michael reaction with acrolein was carried out in MeOH in the presence of 1a. See reference [8b
    • A similar methyl acetal was formed when a catalytic asymmetric Michael reaction with acrolein was carried out in MeOH in the presence of 1a. See reference [8b].


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