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Synlett 1991; 1991(12): 866-867
DOI: 10.1055/s-1991-20905
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Highly Enantioselective Synthesis of Optically Active γ-Substituted 2-Buten-4-olides by Bakers' Yeast Reduction

Sadao Tsuboi* , Jun-ichi Sakamoto, Takashi Sakai, Masanori Utaka
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushima, Okayama 700, Japan
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Publication Date:
07 March 2002 (online)

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Reduction of alkyl 3-chloro-4-oxoalkanoates 1 with Bakers' yeast gave alkyl (4S)-3-chloro-4-hydroxyalkanoates 2, which were hydrolyzed and dehydrochlorinated to give (S)-4-alkyl-2-buten-4-olides 3 with greater than 96 % enantiomeric excess.