Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
نویسندگان
چکیده
The stereoselective Diels-Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.
منابع مشابه
Cysteine-derived organocatalyst in a highly enantioselective intramolecular Michael reaction.
Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.
متن کاملSynthesis and antimicrobial activity of some novel heterocycles containing thiazole, oxazole, thiazine, oxazine and triazole moiety
Indandione 1 was brominated to yield 2-bromoIndandione 2 which on further reacted with substituted thiocarbamides, carbamides, 2-aminothiophenols, 2-aminophenol and triazoles to furnished 3-substituted aniline-2-thia-4-aza-6,7-benzo-8-oxo-bicyclo [3.3.0]-1(5),3-octadiene 3, 3-substituted aniline-2-oxa-4-aza-6,7-benzo-8-oxo-bicyclo [3.3.0]-1(5),3-octadiene 4, 2-Thia-5-aza-9-oxo-3,4-(3’-substitut...
متن کاملAsymmetric Synthesis of Modafinil and its Derivatives by using the Functionalized Silica-based Mesoporous MCM-41
Modafinil [2-[(diphenylmethyl)sulfinyl]acetamide] is used clinically in the treatment of narcolepsy and sleeping disorders. The synthesis of modafinil, begins with the reaction of benzhydrol and thioglycolic acid in trifluoroacetic acid to afford benzhydrylsulfinyl acetic acid. The reaction of acid with thionyl chloride in benzene followed by treatment with ammonium hydroxide gave acetamide...
متن کاملCombining multi-catalysis and multi-component systems for the development of one-pot asymmetric reactions: stereoselective synthesis of highly functionalized bicyclo[4.4.0]decane-1,6-diones.
We have developed a direct amine/acid-catalyzed stereoselective hydrogenation of a variety of Wieland-Miescher (W-M) ketones, Hajos-Parrish (H-P) ketones and their analogs with organic hydrides (Hantzsch esters) as the hydrogen source. This astonishingly simple and biomimetic approach was used to construct highly functionalized chiral bicyclo[4.4.0]decane-1,6-diones in a diastereoselective fash...
متن کاملOne Pot Synthesis of Highly Functionalized Tetrahydropyridines Using Nano-TiCl2/cellulose as Biodegradable and Eco-Friendly Catalyst
TiCl4/nano-cellulose as a biodegradable and eco-friendly Lewis acid catalyst was synthesized via reaction of nano-cellulose and TiCl4. This catalyst was characterized and used for synthesis of asymmetric highly functionalized tetrahydropyridines via a five-component condensation reaction of p-substituted anilines, aldehydes and ethyl acetoacetate under solvent-free condition. Simple methodology...
متن کامل