117993-76-7Relevant articles and documents
Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters
Lai, Luhao,Li, A-Ni,Zhou, Jiawei,Guo, Yarong,Lin, Li,Chen, Wei,Wang, Rui
, p. 2185 - 2190 (2017/03/17)
This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.
Regiochemistry of molybdenum-catalyzed O-H insertions of vinylcarbenoids
Davies, Huw M. L.,Yokota, Yasuno
, p. 4850 - 4854 (2007/10/03)
Molybdenum-catalyzed decomposition of vinyldiazoacetates generates vinylcarbenoids that preferentially react with alcohols at the vinylogous position of the vinylcarbenoid rather than at the carbenoid site.
Reductive Cleavage Reaction of γ-Functionalized α,β-Unsaturated Esters and Halomethyls Mediated with Magnesium in Methanol
Pak, Chwang Siek,Lee, Eun,Lee, Ge Hyeong
, p. 1523 - 1530 (2007/10/02)
Reductive cleavage of various types of C-O and C-N bonds tethered to α,β-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of δ-hydroxy or δ-amino β,γ-unsaturated esters and allylic alcohols.Regardless of the geometry (E or Z) of the α,β-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters.The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.