Stereoselective Synthesis of <i>trans</i>-2,5-Disubstituted Tetrahydrofurans <i>via</i> the Lewis Acid Mediated Reduction of Cyclic Hemiketals with Triphenylsilane

• Yutaka Nishiyama

  Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai UniversitySuita, Osaka

• Takashi Tujino

  Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai UniversitySuita, Osaka

• Tadamichi Yamano

  Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai UniversitySuita, Osaka

• Masayoshi Hayashishita

  Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai UniversitySuita, Osaka

• Kazuyoshi Itoh

  Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai UniversitySuita, Osaka

Abstract

An efficient method for the synthesis of trans-2,5-disubstituted tetrahydrofuran derivatives has been developed. Dithioacetal-functionalized cyclic hemiketals are reduced by triphenylsilane (Ph3SiH) in the presence of TiCl4 to afford the corresponding trans-2,5-disubstituted tetrahydrofuran derivatives in good yield and high stereoselectivity. Asymmetrical synthesis of (2S,5S) disubstituted tetrahydrofuran was also achieved by using this reduction method.

Journal

• Chemistry Letters

  Chemistry Letters 26 (2), 165-166, 1997-02-01

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360565169062737792
• NII Article ID: 10002609864
• NII Book ID: AA00603318
• DOI: 10.1246/cl.1997.165
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/26/2/165/56073659/cl.1997.165.pdf
• Data Source:
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  • CiNii Articles