7236-78-4Relevant articles and documents
Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere
Tang, Yitian,Shen, Chaoren,Yao, Qiyi,Tian, Xinxin,Wang, Bo,Dong, Kaiwu
, p. 5898 - 5902 (2020/10/02)
A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.
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.
Composes heterocycliques spiranniques. V. Synthese et etude configurationnelle dans la serie de l'oxa-2 spirodecane
Picard, Philippe,Moulines, Jean,Lecoustre, Max
, p. 65 - 70 (2007/10/02)
The 8-t-butyl-2-oxaspirodecan-3-one, 8-t-butyl-2-oxaspirodecane and its 3-methylated derivatives were synthesized by different routes starting from methyl 4-t-butylcyclohexanecarboxylate, 4-t-butylmethylenecyclohexane and methyl 4-t-butylcyclohexylidenecyanoacetate.The cis (-CH2O axial) and trans (-CH2O equatorial) isomers were isolated by preparative HPLC ; their configurations were established from (1) the known stereoselectivity of the reaction involved in the cis/trans ratio controlling step (2) their proton and 13C nmr spectra.
