Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives

• Sakamoto Midori

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Kaneko Tetsuya

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Orito Yuya

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Shimoda Yasushi

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Nakajima Makoto

  Graduate School of Pharmaceutical Sciences, Kumamoto University

Abstract

The Michael reaction of malonates with maleates afforded the corresponding adducts in high yields with high enantioselectivities (up to 98% enantiomeric excess (ee)) by using dilithium 3,3′-dichlorobinaphtholate as a catalyst. The obtained Michael adducts could be converted to optically active tricarboxylic acid (TCA) derivatives via the Krapcho reaction.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 67 (5), 452-460, 2019-05-01

  The Pharmaceutical Society of Japan

Keywords

• Michael reaction
• lithium binaphtholate
• tricarboxylic acid ester
• Krapcho reaction
• stereoselectivity

Details

• CRID: 1390564238088348288
• NII Article ID: 130007641166
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c18-00993
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 029658546
• PubMed: 31061370
• Web Site: http://id.ndl.go.jp/bib/029658546
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029658546
• Web Site: https://www.jstage.jst.go.jp/article/cpb/67/5/67_c18-00993/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed