Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes

Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes

The synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under Brønsted base-mediated atmospheric conditions is described. The reaction...

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Bibliographic Details
Main Authors: Tejo, Ciputra, Tirtorahardjo, Davin, Day, David Philip, Ma, Dik-Lung, Leung, Chung-Hang, Chan, Philip Wai Hong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2017
Subjects:
Brønsted Base-mediated
Aziridination
Online Access:https://hdl.handle.net/10356/86641
http://hdl.handle.net/10220/44140
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Institution: Nanyang Technological University
Language: English
Description
Summary:The synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under Brønsted base-mediated atmospheric conditions is described. The reaction mechanism is thought to involve the formal oxidation of the substrate followed by aziridination of the ensuing α,β-unsaturated intermediate by the hypervalent iodine(III) reagent.

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