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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2017
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sg-ntu-dr.10356-866412023-02-28T19:23:40Z Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes Tejo, Ciputra Tirtorahardjo, Davin Day, David Philip Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong School of Physical and Mathematical Sciences Brønsted Base-mediated Aziridination 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. Accepted version 2017-12-13T07:22:13Z 2019-12-06T16:26:22Z 2017-12-13T07:22:13Z 2019-12-06T16:26:22Z 2017 Journal Article Tejo, C., Tirtorahardjo, D., Day, D. P., Ma, D.-L., Leung, C.-H., & Chan, P. W. H. (2017). Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes. Australian Journal of Chemistry, 70(4), 430-435. 0004-9425 https://hdl.handle.net/10356/86641 http://hdl.handle.net/10220/44140 10.1071/CH16580 en Australian Journal of Chemistry © 2017 CSIRO Publishing. This is the author created version of a work that has been peer reviewed and accepted for publication by Australian Journal of Chemistry, CSIRO Publishing. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1071/CH16580]. 5 p. application/pdf |
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| topic |
Brønsted Base-mediated Aziridination |
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Brønsted Base-mediated Aziridination Tejo, Ciputra Tirtorahardjo, Davin Day, David Philip Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes |
| description |
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. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Tejo, Ciputra Tirtorahardjo, Davin Day, David Philip Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong |
| format |
Article |
| author |
Tejo, Ciputra Tirtorahardjo, Davin Day, David Philip Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong |
| author_sort |
Tejo, Ciputra |
| title |
Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes |
| title_short |
Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes |
| title_full |
Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes |
| title_fullStr |
Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes |
| title_full_unstemmed |
Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes |
| title_sort |
brønsted base-mediated aziridination of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds by iminoiodanes |
| publishDate |
2017 |
| url |
https://hdl.handle.net/10356/86641 http://hdl.handle.net/10220/44140 |
| _version_ |
1759855937204518912 |