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

Mugio Nishizawa,* Hiroko Hirakawa, Yuki Nakagawa, Hirofumi Yamamoto, Kosuke Namba and Hiroshi Imagawa

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Email: mugiph.bunri-u.ac.jp

M. Nishizawa, H. Hirakawa, Y. Nakagawa, H. Yamamoto, K. Namba, H. Imagawa, Org. Lett., 2007, 9, 5577-5580.

DOI: 10.1021/ol702548r (free Supporting Information)


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 under very mild reaction conditions with virtually complete E-selectivity.

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Key Words

hydration, unsaturated esters


ID: J54-Y2007-4170