99865-03-9Relevant articles and documents
A Single-Flask Synthesis of Morita-Baylis-Hillman Adducts from Ethoxyacetylene and Carbonyl Compounds: Synthesis of Subamolides D and e
Ng, Kevin,Minehan, Thomas G.
, p. 4028 - 4031 (2016)
Sequential treatment of (ethoxyethynyl)lithium with aldehydes and/or ketones (2 and 4) and BF3·OEt2 gives rise to β-hydroxyenoates 5 in good to excellent overall yields. Similarly, the combination of 1 (M = Li) and dicarbonyl compounds 6 (X = O) or keto/aldehyde acetals (X = OMe) followed by the addition of a Lewis acid leads to five-, six-, and seven-membered hydroxycycloalkene carboxyates. The utility of this method is demonstrated in the synthesis of the α-alkylidene lactone natural products subamolide D and E.
Virtually complete E-selective α,β-unsaturated ester synthesis by Hg(OTf)2-catalyzed hydration of sec-ethoxyalkynyl acetate
Nishizawa, Mugio,Hirakawa, Hiroko,Nakagawa, Yuki,Yamamoto, Hirofumi,Namba, Kosuke,Imagawa, Hiroshi
, p. 5577 - 5580 (2008/09/17)
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.
