29643-77-4Relevant 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 (2019/09/03)
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.
Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester
Chen, Shaojin,Hao, Lin,Zhang, Yuexia,Tiwari, Bhoopendra,Chi, Yonggui Robin
supporting information, p. 5822 - 5825 (2013/12/04)
An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-uns
N-Heterocyclic carbene catalyzed ring expansion of formylcyclopropanes: Synthesis of 3,4-dihydro-α-pyrone derivatives
Li,Dai,You
supporting information; experimental part, p. 1623 - 1625 (2009/09/06)
N-Heterocyclic carbene catalyzed ring expansion of readily accessible 2-acyl-1-formylcyclopropanes was developed. With 5 mol % of triazolium salt 5 and 30 mol % of DBU, ring expansion of various 2-acyl-1-formylcyclopropanes led to 3,4-dihydro-α-pyrones in
Facile synthesis of 3,4-dihydro-α-pyrones via Michael reaction-O-acylation sequences
Kobayashi, Shu,Moriwaki, Mitsuhiro
, p. 551 - 552 (2007/10/03)
3,4-Dihydro-α-pyrones were prepared in excellent yields with high stereoselectivities by the trityl salt-catalyzed Michael reaction and sequential intramolecular O-acylation of the intermediary silyl enol ethers using a mercury (II) salt (one-pot reaction
