Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates

• Shimada Naoyuki

  Faculty of Pharmaceutical Sciences, Hokkaido University

• Nakamura Seiichi

  Faculty of Pharmaceutical Sciences, Hokkaido University

• Anada Masahiro

  Faculty of Pharmaceutical Sciences, Hokkaido University

• Shiro Motoo

  Rigaku Corporation

• Hashimoto Shunichi

  Faculty of Pharmaceutical Sciences, Hokkaido University

Abstract

Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh₂(S-TFPTTL)₄, is an exceptionally efficient catalyst for enantioselective tandem cyclic oxonium ylide formation and [2,3]-sigmatropic rearrangement from α-diazo-β-ketoester bearing cyclic allylic acetal functionality, providing the 2,8-dioxabicyclo[3.2.1]octane core structure of zaragozic acids in up to 93% ee.

Journal

• Chemistry Letters

  Chemistry Letters 38 (5), 488-489, 2009

  The Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1390001204585643776
• NII Article ID: 130004425529
• DOI: 10.1246/cl.2009.488
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/38/5/488/56257058/cl.2009.488.pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed