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Synlett 1991; 1991(11): 811-813
DOI: 10.1055/s-1991-20886
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Remarkable Efficiency in the Catalytic Asymmetric Epoxidation of (E)-3-Trimethylsilyl-2-propen-1-ol

Yuichi Kobayashi* , Takayori Ito, Isao Yamakawa, Hirokazu Urabe, Fumie Sato
  • *Department of Biomolecular Engineering, Toyko Institute of Technology, Meguro, Tokyo 152, Japan
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Publication Date:
07 March 2002 (online)

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The Sharpless epoxidation of (E)-3-trimethylsilyl-2-propen-1-ol (3) affords the corresponding epoxide 4 [(2S,3S)-2, 3-epoxy-3-trimethylsilylpropan-1-ol] in 99% enantiomeric excess in the presence of only 3 mol% of the catalyst (Ti(Oi-Pr)4/L-(+)-diisopropyl tartrate). The epoxide 4 is further converted into various (S)-glycidol [(S)-2, 3-epoxypropan-1-ol] derivatives with retention of optical purity.

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