3-(Phenylseleno)-2-propenal as a versatile unit for oxetane ring formation

Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

“…Vinyl sulfone showed a poorer reactivity as Michael acceptor and a complete inability to cyclize under the standard reaction conditions. A simple synthesis of methoxyoxetanes has been previously described by Kuwajima [28]. In this telescopic protocol, the 1-alkyl-3-phenylseleno-2-propen-1-ols were oxidized with m-CPBA and then treated with NaOH in MeOH.…”

“…A simple synthesis of methoxyoxetanes has been previously described by Kuwajima [ 28 ]. In this telescopic protocol, the 1-alkyl-3-phenylseleno-2-propen-1-ols were oxidized with m -CPBA and then treated with NaOH in MeOH.…”

Ultrasound-Assisted Synthesis of Functionalized 1,3-Enynes by Palladium-Catalyzed Cross-Coupling Reaction of α-Styrylbutyltelluride with Alkynyltrifluoroborate Salts

“…Numerous synthetic methodologies are available for the synthesis of enyne 13 units which involves the chemoselective triple-bond reduction of conjugated unsymmetrical diacetylene systems by using sodium borohydride, 14 flash vacuum pyrolysis of N-propargyloxadiazolinone through a quartz tube, 15 by the reaction of 2-furyllithium with bbromostyrene in the presence of palladium catalyst, 16 and palladium-catalyzed cross-coupling reaction of haloalkenes and haloalkynes with 1-alkenyldisiamylboranes or 1alkenyl-1,3,2-benzodioxaboroles in the presence of bases such as sodium alkoxides. 17 In last decade Montevecchi and his research group reported the synthesis of enynes by DDQ-prompted oxidation of phenylalkylacetylenes.…”

Highly efficient method for ethylenic or acetylenic ketones via fragmentation of hydroxy vinyl selenones

“…When l-butyl-3-(phenylselenonyl)-2-cyclohexen-l-ol (1) was treated with sodium methoxide in methanol at room temperature overnight and then at 45 °C for 3 h, 10methoxy-9-decen-5-one (2) was obtained in 86% yield.5 This reaction proceeds most probably via the conjugate addition of methoxide6 to vinyl selenones followed by a 1,4-fragmentation reaction. This type of reaction (type A) was observed in the reaction of 1 with alkoxides (methoxide, ethoxide) and benzenethiolate to give 1,6-dicarbonyl derivatives in good to excellent yields.…”