4258-42-8Relevant academic research and scientific papers
Reinventing the de Mayo reaction: Synthesis of 1,5-diketones or 1,5-ketoesters via visible light [2+2] cycloaddition of β-diketones or β-ketoesters with styrenes
Martinez-Haya, Rebeca,Marzo, Leyre,K?nig, Burkhard
, p. 11602 - 11605 (2018)
A visible light mediated De Mayo reaction between 1,3-diketones and styrenes following a [2+2] cycloaddition pathway via a photosensitization mechanism gives access to 1,5-diketones. The reaction has been applied to substituted styrenes and aryl- and alkyl-substituted ketones. Moreover, the method converts β-ketoesters, β-amido esters, and β-cyano ketones. Seven membered rings, a frequent structural motif of natural products, are also accessible using this methodology.
Iodine(III)-Mediated Contraction of 3,4-Dihydropyranones: Access to Polysubstituted γ-Butyrolactones
Dagenais, Robin,Lussier, Tommy,Legault, Claude Y.
supporting information, p. 5290 - 5294 (2019/09/03)
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.
