One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction
نویسندگان
چکیده
We report here an efficient one-pot method for the synthesis of α,β-differentiated diamino esters directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed by an intermolecular SN2 nucleophilic ring opening by benzylamine. The reactions feature a wide scope of substrates and proceed with excellent stereo- and regioselectivity (anti:syn >99:1) .
منابع مشابه
Trichloroacetic Acid as an Efficient Catalyst for One-pot Synthesis of Highly Functionalized Piperidines via multi-component Reaction
Trichloroacetic Acid (TCA) was used as an efficient catalyst for the synthesis of highly functionalized piperidines via a one-pot five-component reaction of aromatic amines, aromatic aldehydes and β-keto esters in MeOH at room temperature. The remarkable advantages offered by this method are good yields, simple procedure, short reaction times, no need to column chromatography and an easy wo...
متن کاملAsymmetric synthesis of γ-chloro-α,β-diamino- and β,γ-aziridino-α-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across α-chloro-N-sulfinylimines
The asymmetric synthesis of new chiral γ-chloro-α,β-diaminocarboxylamide derivatives by highly diastereoselective Mannich-type reactions of N-(diphenylmethylene)glycinamides across chiral α-chloro-N-p-toluenesulfinylaldimines was developed. The resulting (S(S),2S,3S)-γ-chloro-α,β-diaminocarboxylamides were formed with the opposite enantiotopic face selectivity as compared to the (S(S),2R,3R)-γ-...
متن کاملZrP2O7 NPs: A recyclable, efficient heterogeneous catalyst for the synthesis of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via a multi-component reaction
ZrP2O7 nanoparticles (NPs) as an efficient catalyst have been used for the preparation of 1,6-diamino-2- oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via one-pot coupling of hyrazine hydrate, ethyl cyanoacetate, malononitrile and aromatic aldehydes under reflux conditions in ethanol. Using this method we obtained low reaction times, easy isolation of the targeted molecules, e...
متن کاملZrP2O7 NPs: A recyclable, efficient heterogeneous catalyst for the synthesis of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via a multi-component reaction
ZrP2O7 nanoparticles (NPs) as an efficient catalyst have been used for the preparation of 1,6-diamino-2- oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via one-pot coupling of hyrazine hydrate, ethyl cyanoacetate, malononitrile and aromatic aldehydes under reflux conditions in ethanol. Using this method we obtained low reaction times, easy isolation of the targeted molecules, e...
متن کاملNew Methods for the Synthesis of Vicinal Stereocenters: Palladium-Catalyzed Domino Reactions and Asymmetric Transfer Hydrogenation
In this thesis the synthesis of vicinal stereocenters is investigated in two distinct contexts, namely the construction of 3,3-disubstituted oxindoles and the synthesis of β-hydroxy-α-amino acids. Both scaffolds are prevalent in a range of natural products and biologically relevant compounds and, therefore, methods for their synthesis are of great import. First, the construction of 3,3-disubsti...
متن کامل