99046-13-6Relevant 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
supporting information, 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.
Stereoselective Reduction of γ-Oxobutanoic Acids Using DIBAL-H and ZnCl2
Frenette, R.,Monette, M.,Bernstein, M. A.,Young, R. N.,Verhoeven, T. R.
, p. 3083 - 3089 (2007/10/02)
A variety of γ-aromatic γ-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-γ-aryl-γ-hydroxy-β-methylbutanoic acids.Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity.Also we have shown that some γ-aryl-γ-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.