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...

全面介紹

Saved in:
書目詳細資料
Main Authors: Ton, Thi My Uyen, Tejo, Ciputra, Tiong, Diane Ling Ying, Chan, Philip Wai Hong
其他作者: School of Physical and Mathematical Sciences
格式: Article
語言:English
出版: 2013
在線閱讀:https://hdl.handle.net/10356/95911
http://hdl.handle.net/10220/11286
標簽: 添加標簽
沒有標簽, 成為第一個標記此記錄!
機構: Nanyang Technological University
語言: English
實物特徵
總結: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.