Study on the stereoselective construction of furans with an asymmetric quaternary center at the 2-position

DOI
  • Sashihara Yoshiaki
    Department of Chemistry, Graduate School of Science, Hiroshima University
  • Iwamoto Akihisa
    Department of Chemistry, Graduate School of Science, Hiroshima University
  • Kojima Satoshi
    Department of Chemistry, Graduate School of Science, Hiroshima University Center for Quantum Life Science, Hiroshima University
  • Abe Manabu
    Department of Chemistry, Graduate School of Science, Hiroshima University

Bibliographic Information

Other Title
  • ２位に不斉四級炭素を有するフラン環の立体選択的構築に関する研究

Description

During our examination on the generality of the asymmetric Michael reaction using a chiral piperazine, we found that furans bearing a quaternary carbon center at the 2-position could be constructed just by mixing 2-oxo-cyclopentanecarboxylic acid benzyl ester and (Z)-4-oxo-pent-2-enal in the presence of weak Bronsted acids such as HFIP and carboxylic acids . Since the reaction proceeded under mild conditions, the diastereoselective furan formation reaction was examined by using B-ketoesters bearing chiral auxiliaries. As a result, it was found that high diastereoselectivity could be achieved by using 8-phenylmenthol as the chiral auxiliary with selectivity as high as 96% de. Determination of the stereochemistry of the major diastereomer and the examination of the generality of this diastereoselective reaction are currently underway.

Journal

Keywords

Details 詳細情報について

  • CRID
    1390001205554842624
  • NII Article ID
    130004645253
  • DOI
    10.11494/kisoyuki.2008.0.145.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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