Asymmetric Aldol/Vinylogous Aldol/Cyclization Reaction Using Phosphine Oxide Catalysts

• Alim Nathan Ray

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Miyazaki Shiki

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Shimoda Yasushi

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Sugiura Masaharu

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Nakajima Makoto

  Graduate School of Pharmaceutical Sciences, Kumamoto University

• Kotani Shunsuke

  Graduate School of Pharmaceutical Sciences, Kumamoto University Priority Organization for Innovation and Excellence, Kumamoto University

Abstract

Chiral phosphine oxide sequentially activates silicon tetrachloride and trichlorosilyl enol ethers to facilitate asymmetric aldol/vinylogous aldol reaction of 4-methoxy-3-penten-2-one and conjugated aldehydes in a highly enantioselective fashion, and the subsequent cyclization produced optically active 2,6-disubstituted 2,3-dihydro-4-pyranones bearing stereogenic centers at a remote position in a single operation.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 65 (10), 989-993, 2017

  The Pharmaceutical Society of Japan

Keywords

• phosphine oxide
• pyranone
• asymmetric catalysis
• tandem reaction
• remote-control

Details

• CRID: 1390001204178318080
• NII Article ID: 130006109936
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c17-00540
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 028540761
• PubMed: 28966283
• Web Site: http://id.ndl.go.jp/bib/028540761
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I028540761
• Web Site: https://www.jstage.jst.go.jp/article/cpb/65/10/65_c17-00540/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed