Virtually Complete E-Selective α,β-Unsaturated Ester Synthesis by Hg(OTf)₂-Catalyzed Hydration of sec-Ethoxyalkynyl Acetate

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Abstract

The reaction of alkyl-substituted sec-ethoxyalkynyl acetates with water catalyzed by Hg(OTf)₂ afforded α,β-unsaturated esters in excellent yield with high catalytic turnover up to 1000 times under very mild reaction conditions with virtually complete E-selectivity, superior even to that of the HWE reaction.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

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  Mo−Au Combo Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols into α,β-Unsaturated Carbonyl Compounds

  Masahiro Egi, Yoshiko Yamaguchi, Noboru Fujiwara and Shuji Akai
  Organic Letters2008 10 (9), 1867-1870

  • Mo−Au Combo Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols into α,β-Unsaturated Carbonyl Compounds

    Masahiro Egi, Yoshiko Yamaguchi, Noboru Fujiwara and Shuji Akai
    Organic Letters2008 10 (9), 1867-1870

    The combination of Mo and cationic Au catalysts dramatically accelerated the rearrangement of diverse propargyl alcohols, which includes a short reaction time, mild conditions, and high product yields. A practical application to the highly challenging ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Hg(OTf)₂-Catalyzed Arylene Cyclization

  Kosuke Namba, Hirofumi Yamamoto, Ikuo Sasaki, Kumiko Mori, Hiroshi Imagawa and Mugio Nishizawa
  Organic Letters2008 10 (9), 1767-1770

  • Hg(OTf)₂-Catalyzed Arylene Cyclization

    Kosuke Namba, Hirofumi Yamamoto, Ikuo Sasaki, Kumiko Mori, Hiroshi Imagawa and Mugio Nishizawa
    Organic Letters2008 10 (9), 1767-1770

    Novel Hg(OTf)2-catalyzed arylene cyclization was achieved with highly efficient catalytic turnover (up to 200 times). The reaction takes place via protonation of allylic hydroxyl group by in situ formed TfOH of an organomercuric intermediate to generate ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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