53560-49-9Relevant articles and documents
Solid-phase organic synthesis of 5-iodomethyl-dihydrofuran-2-ones with recyclable polymer-supported selenium bromide
Wang, Chao-Li,Sheng, Shou-Ri.,Cheng, Xin,Cai, Ming-Zhong
, p. 320 - 327 (2012)
Reaction of polystyrene-supported selenium bromide with γ,δ-unsaturated acids and subsequent cleavage from the polymer by treatment with methyl iodide efficiently afforded 5-iodomethyl-dihydrofuran-2- ones in excellent yields. The polymeric reagent can be regenerated and reused as an environmentally friendly reagent. Copyright Taylor & Francis Group, LLC.
Synthesis of β,β-disubstituted γ-butyrolactones by chemo-selective oxidation of 1,4-diols and γ-hydroxy olefins with rucl3/NaIO4
Gao, Rong,Fan, Rong,Canney, Daniel J.
supporting information, p. 661 - 665 (2015/03/14)
Substituted γ-butyrolactones represent an important group of structural fragments commonly found in natural products, receptor ligands, and drug molecules. Interest in preparing a library of substituted γ-butyrolactones and finding that limited routes to β-substituted lactones exist, led to the development of an efficient approach for the synthesis of β,β-disubstituted γ-butyrolactones. Readily prepared substituted 1,4-diols and γ-hydroxy olefins were treated with the -RuCl3/NaIO4 oxidation system to provide the target β,β-disubstituted γ-butyrolactones in modest to good yields. The reaction goes through a lactol intermediate that was isolated and characterized for selected compounds. The approach supplies an efficient and versatile method for the synthesis of these important heterocyclic structures. Importantly, the present work is the first report that demonstrates the ability of RuCl3/NaIO4 to selectively oxidize primary hydroxyl groups in the presence of secondary alcohols to prepare lactones in good yields.
Regioselective (Diacetoxyiodo)benzene-promoted halocyclization of unfunctionalized olefins
Liu, Gong-Qing,Li, Yue-Ming
, p. 10094 - 10109 (2015/02/19)
A metal-free method for intramolecular halocyclization of unfunctionalized olefins was detailed. (Diacetoxyiodo)benzene (PIDA) was very effective for haloamidation, haloetherification, and halolactonization of unfunctionalized olefins. In the presence of
