One-pot Aziridination Research Articles

An efficient synthesis of substituted hexahydrobenzo[f]thieno[c]quinoline; an advanced intermediate of analog of A-86929, a dopamine D1 full agonist

An efficient synthesis of substituted hexahydrobenzo[ f]thieno[ c]quinolines was achieved via catalytic one-pot aziridination followed by Friedel–Crafts cyclization and a mild Pictet–Spengler cyclization protocol. Cu(OTf)2was an effective catalyst for both aziridination followed by Friedel–Crafts cyclization with excellent diastereoselectivity (dr: >99:1) and high yield (75%).

Synthesis and Structure of Hypervalent Diacetoxybromobenzene and Aziridination of Olefins with Imino-λ3-bromane Generated in Situ under Metal-Free Conditions

Ligand exchange of p-CF(3)C(6)H(4)BrF(2) with acetoxy groups using AcOH and Ac(2)O affords (diacetoxybromo)benzene in a high yield, which undergoes aziridination of alkenes in the presence of TfNH(2) and sulfamate esters in one pot under mild conditions. The aziridination with TfNH(2) proceeds stereospecifically with retention of stereochemistry of olefins at room temperature using limiting amounts of olefins under transition-metal-free conditions. The one-pot aziridination procedure using sulfamate esters can be applied to the intramolecular versions.

Catalytic enantioselective synthesis of A-86929, a dopamine D1 agonist

A-86929, a dopamine D1 agonist was synthesized with 95% ee in five steps with overall yield of 56% via catalytic enantioselective one-pot aziridination followed by Friedel-Crafts cyclization and a mild Pictet-Spengler cyclization protocol.

Substrate-Induced Covalent Assembly of a Chemzyme and Crystallographic Characterization of a Chemzyme−Substrate Complex

A substrate induced covalent assembly of a highly organized chemzyme known to be effective in both catalytic asymmetric aziridination and aza Diels-Alder reactions is described and the information gained from which led to an efficient one-pot aziridination protocol. The crystal structures of two chemzyme-iminium complexes were elucidated by X-ray diffraction analysis that provides critical insights into the binding of the substrates with the chemzyme.

A one-pot stereoselective synthesis of trans-1-aryl-2-aminotetralins from 2-arylethyl styrenes

An efficient stereoselective synthesis of trans-1-aryl-2-aminotetralins has been achieved via Cu(OTf) 2 catalyzed one-pot aziridination and regioselective intramolecular arylation of in situ generated aziridines from 2-arylethyl styrenes and PhINSO 2(4-NO 2C 6H 4) [PhINNs]. Reaction of a mixture of E/ Z-styrenes (⩽85:15) provided trans-N-protected-1-aryl-2-aminotetralins with high diastereoselectivity (dr > 95:5), which are important synthons for many artificial pharmaceuticals.

Copper(I)‐Catalyzed Asymmetric Alkene Aziridination Mediated by PhI(OAc)2: A Facile One‐Pot Procedure.

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Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc) 2: a facile one-pot procedure

A facile one-pot procedure for copper-catalyzed PhI(OAc) 2-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc) 2 and sulfonamides were used to generate the nitrene precursors (PhINR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5 mol % of the chiral copper catalyst, these conditions afforded 94% yield of the isolated product with 75% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination.

Enantioselective synthesis of aziridines from imines and alkyl halides using a camphor-derived chiral sulfide mediator via the imino Corey–Chaykovsky reaction

Asymmetric one-pot aziridination of imines with alkyl bromides via the imino Corey–Chaykovsky reaction mediated by chiral sulfide is described. The desired aziridines are obtained in good yields with up to 98% ee of the trans isomer.