Stereoselective Synthesis of trans-2, 5-Disubstituted Tetrahydrofurans via the Lewis Acid Mediated Reduction of Cyclic Hemiketals with Triphenylsilane
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An efficient method for the synthesis of <I>trans</I>-2,5-disubstituted tetrahydrofuran derivatives has been developed. Dithioacetal-functionalized cyclic hemiketals are reduced by triphenylsilane (Ph<SUB>3</SUB>SiH) in the presence of TiCl<SUB>4</SUB> to afford the corresponding <I>trans</I>-2,5-disubstituted tetrahydrofuran derivatives in good yield and high stereoselectivity. Asymmetrical synthesis of (2<I>S</I>,5<I>S</I>) disubstituted tetrahydrofuran was also achieved by using this reduction method.
- Chemistry Letters
Chemistry Letters 1997(2), 165-166, 1997-02
The Chemical Society of Japan