Enantioselective Aldol Reaction of Trimethoxysilyl Enol Ethers Catalyzed by Lithium Binaphtholate

• Nakajima Makoto

  Graduate School of Pharmaceutical Sciences, Hokkaido University

• Orito Yuya

  Graduate School of Pharmaceutical Sciences, Hokkaido University

• Hashimoto Shunichi

  Graduate School of Pharmaceutical Sciences, Hokkaido University

Bibliographic Information

Other Title

• リチウムビナフトラートを触媒とするトリメトキシシリルエノールエーテルの不斉アルドール反応

Abstract

The aldol reaction is one of the most powerful methods of forming carbon–carbon bonds. We found that lithium binaphtholates are effective catalysts for the aldol reaction of trimethoxysilyl enol ethers with aldehydes. The aldol reaction of trimethoxysilyloxycyclohexene and benzaldehyde catalyzed by lithium binaphtholate (10 mol%) prepared from (R)-3,3'-dichloro-2,2'-binaphthol and n-BuLi afforded the corresponding anti-adduct predominantly in high yield with 56% ee. Though the enantioselectivities are still modest, the present reaction is the first example of base-catalyzed enantioselective aldol reaction of trimethoxysilyl enol ethers with carbonyl compounds.

Journal

• Proceedings of the Symposium on Progress in Organic Reactions and Syntheses

  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses 29 (0), 206-207, 2003

  Division of Organic Chemistry, The Pharmaceutical Society of Japan

Keywords

• aldol reaction
• chiral catalyst
• enantioselective
• lithium binaphtholate

Details

• CRID: 1390001205634760448
• NII Article ID: 130006997193
• DOI: 10.14895/hannou.29.0.206.0
• Data Source:
  • JaLC
  • CiNii Articles
• Abstract License Flag: Disallowed