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Synlett 1993; 1993(11): 855-857
DOI: 10.1055/s-1993-22632
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Aluminum Triflate-Mediated Aldol Reactions. Stereoselective Synthesis of Both Diastereomers Including the α-Alkoxy-β-hydroxy-β-methyl Units.

Shū Kobayashi* , Mineko Horibe
  • *Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Kagurazaka, Shinjuku-ku, Tokyo 162, Japan
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Publication Date:
19 March 2002 (online)

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Both diastereomers including the syn- and anti-α-alkoxy-β-hydroxy-β-methyl units are prepared from (E)- and (Z)-1-trimethylsiloxy-1-ethylthio-2-benzyloxyethene and a pyruvic acid ester, respectively, by using aluminum triflate-mediated aldol reactions. (±)-2-C-Methyl-D-erythrono-1,4-lactone and (±)-2-C-methyl-D-threono-1,4-lactone are synthesized by using these reactions.