Stereoselective one-pot synthesis of β-alkylsulfide enol esters. Base-triggered rearrangement under mild conditions.
نویسندگان
چکیده
A stereoselective one-pot procedure was developed to prepare S-substituted (Z)-enol esters through a base-triggered rearrangement. This transition metal-free multicomponent approach can be performed under an air atmosphere at room temperature, tolerates a wide set of chemical functionalities and generally affords high isolated yields. The (Z)-selectivity arises from the [1,4]-S- to O-acyl migration.
منابع مشابه
Novel one-pot synthesis of diverse γ,δ-unsaturated β-ketoesters by thermal cascade reactions of diazodicarbonyl compounds and enol ethers: transformation into substituted 3,5-diketoesters.
Sequential Wolff rearrangement of α-diazo-β-ketoesters followed by trapping of the ketene intermediates with enol ethers generated a variety of γ,δ-unsaturated β-ketoesters. This method involves a novel thermal cascade reaction and allows the synthesis of γ,δ-unsaturated β-ketoesters with trans-stereochemistry under catalyst-free conditions. The synthesized compounds were further transformed in...
متن کاملHighly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes
We report the highly efficient gold-catalyzed hydrocarboxylation of internal alkynes that operates under solvent- and silver-free conditions. This new, simple, and eco-friendly protocol allows for the synthesis of a wide variety of functionalized aryl and alkyl enol esters in high yields, with Z-stereospecificity and good regioselectivities and without the requirement for purification by chroma...
متن کاملAn Efficient Synthesis of 3,4-Dihydropyrimidin-2-(1H)-one Derivatives Promoted by Antimony Trichloride under Thermal and Solvent-free Conditions
An efficient and simple one-pot approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives using antimony trichloride (SbCl3) as a mild catalyst by means of three-component Biginelli reaction between β-keto esters, aldehyde derivatives and urea/thiourea under thermal and solvent-free conditions with excellent yields and short reaction times is reported. This m...
متن کاملOne-pot Efficient Oximation-Beckmann Rearrangement of Ketones Catalyzed by Fe3O4 Under Solvent-free Conditions
Fe3O4 nanoparticles were employment as an efficient and magnetically separable Nano catalyst for the synthesis of amides via one-pot Beckmann rearrangement of ketones under solvent-free conditions. Various secondary amides were synthesized by this method in moderate to good yields. The catalyst showed high thermal stability and was recovered and reused at least five times without any considerab...
متن کاملOxalic acid dihydrate catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives under thermal and solvent-free conditions
Oxalic acid dihydrate as a green, mild and efficient catalyst for the one-pot three-component Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives from the reaction between β-keto esters (methyl or ethyl acetoacetate), aromatic aldehyde (benzaldehye derivatives) and urea or thiourea under thermal and solvent-free conditions with excellent yields and short reaction time is st...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 12 33 شماره
صفحات -
تاریخ انتشار 2014