Virtually complete E-selective alpha,beta-unsaturated ester synthesis by Hg(OTf)2-catalyzed hydration of sec-ethoxyalkynyl acetate.
The reaction of alkyl-substituted sec-ethoxyalkynyl acetates with water catalyzed by Hg(OTf)2 afforded alpha,beta-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.
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. mugi@ph.bunri-u.ac.jp
Mugio
M
Nishizawa
Hiroko
H
Hirakawa
Yuki
Y
Nakagawa
Hirofumi
H
Yamamoto
Kosuke
K
Namba
Hiroshi
H
Imagawa
D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D017669:Mercury Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000085:Acetates; D004952:Esters; D017669:Mercury Compounds; D014867:Water