Enantioselective direct aldol reaction of α-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions.
نویسندگان
چکیده
(S(a))-Binam-D-prolinamide (20 mol%), instead of (S(a))-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between α-keto esters as electrophiles and alkyl and α-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary γ-keto α-hydroxyesters with up to 92% ee.
منابع مشابه
Enantioselective solvent-free synthesis of 3-alkyl-3-hydroxy-2-oxoindoles catalyzed by binam-prolinamides.
BINAM-prolinamides are very efficient catalyst for the synthesis of non-protected and N-benzyl isatin derivatives by using an aldol reaction between ketones and isatins under solvent-free conditions. The results in terms of diastereo- and enantioselectivities are good, up to 99% de and 97% ee, and higher to those previously reported in the literature under similar reaction conditions. A high va...
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 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 کامل(Carboxy-3-oxopropylamino)-3-propylsilylcellulose as a novel organocatalyst for the synthesis of coumarin derivatives under solvent-free conditions
In this research, (Carboxy-3-oxopropylamino)-3-propylsilylcellulose (COPAPSC) as an organocatalyst, has been synthesized by grafting of succinic anhydride on the NH2-modified cellulose (cellulose functionalized with 3- aminopropyltriethoxysilane). The –CO2H group-functionalized cellulose (COPAPSC) is used as a catalyst for the synthesis of coumarin derivatives from the reaction of phenolic subs...
متن کاملSynthesis of electron-poor N-Vinylimidazole derivatives catalyzed by Silica nanoparticles under solvent-free conditions
Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and acetylenic esters, by NH-acids such as azathioprine, imidazole or theophylline leads to the formation of vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce phosphorus ylides. Silica nanoparticles (silica NPs were prepared by therm...
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 10 20 شماره
صفحات -
تاریخ انتشار 2012