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Synlett 1992; 1992(4): 325-327
DOI: 10.1055/s-1992-22001
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Protected Vicinal Diol Controller in Diastereoselective Reduction of ß-Oxo Esters

Seiki Saito* , Takeshi Harunari, Nobuhiro Shimamura, Masahiro Asahara, Toshio Moriwake
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 3-1-1 Tsushima-naka, Okayama 700, Japan
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Publication Date:
08 March 2002 (online)

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A protected vicinal diol controller has proven to be highly effective for the diastereoselective reduction of a carbonyl group in ß-oxo esters linked to the controller unit. For example, ethyl (E,4R,5S)-8-acetoxy-4,5-bis (tert-butyldimethylsiloxy)-3-oxo-6-octenoate (2a) was converted into the corresponding 3R alcohol 3a in >99% diasteromeric excess.