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Synlett 1993; 1993(9): 645-646
DOI: 10.1055/s-1993-22555
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Regio- and Stereocontrol in the Reductive Ring Opening of the Spirocyclic Epoxide Derived from the 4-Siloxy-2-cyclopentenone

Katsuhiko Tomooka* , Katsuya Ishikawa, Md. Al-Masum, Takeshi Nakai
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan
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Publication Date:
19 March 2002 (online)

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Reductions of the title epoxide with DIBAL, NaBH4, and LiBEt3H are shown to afford the cis-3-hydroxymethyl-5-siloxy-1-cyclopentene, 2-hydroxymethyl-4-siloxy-1-cyclopentene, and the 1-methyl-4-siloxy-2-cyclopentene-1-ol, respectively, in a high selectivity.

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