16720-76-6Relevant articles and documents
Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones
Kiyokawa, Kensuke,Takemoto, Kenta,Yahata, Shunsuke,Kojima, Takumi,Minakata, Satoshi
supporting information, p. 2907 - 2912 (2017/06/27)
The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf) 2, which is in situ prepared from PhI(OAc) 2 and Me 3 SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5 H)-ones or furan-2(3 H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.
Preparation and reactions of 3,4-bisstannyl-2(5H)furanones
Carter, Neil B,Mabon, Ross,Richec?ur, Alexandre M.E,Sweeney
, p. 9117 - 9129 (2007/10/03)
Bistributylstannyl-2(5H)-furanone 4a has been prepared from 3-(tetrahydropyran-2-yl)oxy but-2-ynoate and shown to exhibit good selectivity in its Stille reactions with a range of halogenated compounds, leading to 4-substituted-3-stannyl-2(5H)-furanones, in generally moderate yield. Under certain reaction conditions, doubly substituted products were also isolated from the reactions. The 3,4-bistrimethylstannyl furanone, 4b, corresponding to 4a was prepared, but decomposed during all attempts to execute Stille reactions upon it.
3-Phenylselanylfuran-2(5H)-one: A versatile building block in the synthesis of lignans. A new approach towards 3,4-dibenzyl γ-butyrolactones
Bella, Marco,Piancatelli, Giovanni,Pigro, Maria Cristina
, p. 12387 - 12398 (2007/10/03)
Ready available 3-phenylselanylfuran-2(5H)-one undergoes tandem conjugate addition-alkylation by organocopper reagents to afford, with good yields and diastereoselectivities, 3,4-disubstituted-3-phenylselanyl-γ- butyrolactones, which can be transformed into naturally occurring compounds, such as lignans.