134931-80-9Relevant academic research and scientific papers
Iodine(III)-Mediated Contraction of 3,4-Dihydropyranones: Access to Polysubstituted γ-Butyrolactones
Dagenais, Robin,Lussier, Tommy,Legault, Claude Y.
, p. 5290 - 5294 (2019)
Functionalized γ-butyrolactones are privileged structures in the field of medicinal chemistry; they are found in numerous natural products and synthetic compounds with diverse biological activities. The oxidative ring contraction of 3,4-dihydropyran-2-one derivatives represents a promising yet underappreciated strategy to access these compounds. To the best of our knowledge, very few examples of this strategy have been reported, with limited investigation of the influence of stereogenic centers on the starting dihydropyranones. We investigated the iodine(III)-mediated contraction of a representative set of dihydropyranone derivatives. The method gives rapid access to functionalized γ-butyrolactones in good yields. The reaction scope was investigated, and the method was found to support various levels of substituents, even enabling access to sterically congested quaternary centers. The stereoselectivity was investigated using chiral substrates and a chiral iodine(III) reagent.
A novel Michael reaction of silyl enol ethers via hetero Diels-Alder reaction with Alkylidene-Meldrum's acid
Mizukami,Kihara,Endo
, p. 7437 - 7440 (2007/10/02)
Alkylidene Meldrum's acid easily reacted with silyl enol ethers without any catalyst to afford hetero Diels-Alder adducts which could be quantitatively hydrolyzed to obtain Michael adducts in good yields. The Michael adducts could be obtained diastereoselectively and could be converted to corresponding δ-ketoesters quantitatively.
