Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds

A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)2 + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI═NTs is described. By taking advantage of the orthogonal modes of rea...

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Main Authors: Ton, Thi My Uyen, Tejo, Ciputra, Tiong, Diane Ling Ying, Chan, Philip Wai Hong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/95911
http://hdl.handle.net/10220/11286
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-959112020-03-07T12:37:22Z Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds Ton, Thi My Uyen Tejo, Ciputra Tiong, Diane Ling Ying Chan, Philip Wai Hong School of Physical and Mathematical Sciences A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)2 + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI═NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C—H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the β-aminated adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2–3 equiv was discovered to result in preferential formal aziridination of the C—C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product. 2013-07-12T03:20:11Z 2019-12-06T19:23:16Z 2013-07-12T03:20:11Z 2019-12-06T19:23:16Z 2012 2012 Journal Article Ton, T. M. U., Tejo, C., Tiong, D. L. Y., & Chan, P. W. H. (2012). Copper(II) Triflate Catalyzed Amination and Aziridination of 2-Alkyl Substituted 1,3-Dicarbonyl Compounds. Journal of the American Chemical Society, 134(17), 7344-7350. https://hdl.handle.net/10356/95911 http://hdl.handle.net/10220/11286 10.1021/ja301415k en Journal of the American chemical society © 2012 American Chemical Society.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
description A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)2 + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI═NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C—H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the β-aminated adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2–3 equiv was discovered to result in preferential formal aziridination of the C—C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ton, Thi My Uyen
Tejo, Ciputra
Tiong, Diane Ling Ying
Chan, Philip Wai Hong
format Article
author Ton, Thi My Uyen
Tejo, Ciputra
Tiong, Diane Ling Ying
Chan, Philip Wai Hong
spellingShingle Ton, Thi My Uyen
Tejo, Ciputra
Tiong, Diane Ling Ying
Chan, Philip Wai Hong
Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
author_sort Ton, Thi My Uyen
title Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
title_short Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
title_full Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
title_fullStr Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
title_full_unstemmed Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
title_sort copper(ii) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
publishDate 2013
url https://hdl.handle.net/10356/95911
http://hdl.handle.net/10220/11286
_version_ 1681041501106208768