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

หน่วยงาน Nanyang Technological University, Singapore

รายละเอียด

ชื่อเรื่อง : Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds
นักวิจัย : Ton, Thi My Uyen , Tejo, Ciputra , Tiong, Diane Ling Ying , Chan, Philip Wai Hong
คำค้น : -
หน่วยงาน : Nanyang Technological University, Singapore
ผู้ร่วมงาน : -
ปีพิมพ์ : 2555
อ้างอิง : 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. , http://hdl.handle.net/10220/11286 , http://dx.doi.org/10.1021/ja301415k
ที่มา : -
ความเชี่ยวชาญ : -
ความสัมพันธ์ : Journal of the American chemical society
ขอบเขตของเนื้อหา : -
บทคัดย่อ/คำอธิบาย :

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.

บรรณานุกรม :
Ton, Thi My Uyen , Tejo, Ciputra , Tiong, Diane Ling Ying , Chan, Philip Wai Hong . (2555). Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds.
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Ton, Thi My Uyen , Tejo, Ciputra , Tiong, Diane Ling Ying , Chan, Philip Wai Hong . 2555. "Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds".
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
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."
    กรุงเทพมหานคร : Nanyang Technological University, Singapore, 2555. Print.
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. กรุงเทพมหานคร : Nanyang Technological University, Singapore; 2555.