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Synlett 1999; 1999(5): 547-548
DOI: 10.1055/s-1999-2685
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Effects of Metal Cations in Lewis Acid-Surfactant Combined Catalyst-Mediated Aldol Reactions in Water

Kei Manabe* , Shū Kobayashi
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Fax +81(3)56 84 06 34; E-mail: skobayas@mol.f.u-tokyo.ac.jp
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Publikationsdatum:
31. Dezember 1999 (online)

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Studies on aldol reactions of benzaldehyde with a thioketene silyl acetal in water in the presence of various dodecyl sulfate and dodecanesulfonate salts as Lewis acid-surfactant combined catalysts have revealed that the order of the catalytic ability of these salts at the initial stage of the reaction is Cu > Zn, Ag > Sc, Yb > Na > Mn, Co salts, and that the Sc and Yb salts afforded the aldol product in more than 90% final yields due to their ability to suppress the hydrolysis of the thioketene silyl acetal.

Lewis acid - aldol reaction - surfactant - metal cation - thioketene silyl acetal