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

2007; American Chemical Society; Volume: 9; Issue: 26 Linguagem: Inglês

10.1021/ol702548r

1523-7060

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

Chemical Synthesis and Analysis

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.