108350-21-6Relevant articles and documents
An efficient procedure for the synthesis of formylacetic esters
Edvinsson, Sofie,Johansson, Susanne,Larsson, Andreas
, p. 6819 - 6821 (2012)
An efficient synthesis of formylacetic esters via ozonolysis of trans-β-hydromuconic esters followed by a solid-supported triphenylphosphine reduction has been developed. In addition, an extension toward formylacetic amides and a one-pot preparation of more stable intermediates which can be used for further transformations are also described.
Scope and diastereoselectivity of the interrupted Feist-Benary reaction.
Calter, Michael A,Zhu, Cheng
, p. 205 - 208 (2002)
[reaction: see text] The base-promoted condensation of beta-dicarbonyl compounds with alpha-haloketones, the Feist-Benary reaction, conveniently produces highly substituted dihydrofurans. We show here that this reaction is quite general with respect to the nature of the beta-dicarbonyl compound, proceeding with beta-ketoesters, beta-oxopropionates, beta-diketones, and beta-dialdehydes. We also show that the diastereoselectivity of this reaction depends on the acidity of the nucleophile.
NHC catalyzed enantioselective Coates-Claisen rearrangement: A rapid access to the dihydropyran core for oleuropein based secoiridoids
Vedachalam, Seenuvasan,Murugesh, Nithya,Chakraborty, Priyanka,Karvembu, Ramasamy,Liu, Xue-Wei
supporting information, p. 1832 - 1839 (2018/02/09)
We present the short synthesis of the suitably functionalized enantioselective dihydropyran core of secoiridoids using an N-heterocyclic carbene (NHC) catalyzed Coates-Claisen rearrangement mechanism. The key steps of the synthesis are (i) the highly enantioselective NHC catalyzed Coates-Claisen rearrangement for the dihydropyran core, (ii) the assembly of the target dihydropyran core structure of oleuropein from a highly diastereoselective exocyclic trans alkene, and (iii) the highly stereoselective assembly of a monoterpene elenolide core structure.
