Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts?
Organic & Biomolecular Chemistry Pub Date: 2017-05-30 DOI: 10.1039/C7OB00799J
Abstract
Herein we report a two-step sequence for the preparation of amides starting from azides and enolisable aldehydes. The reaction proceeded via the formation of triazoline intermediates that were converted into amides via Lewis acid catalysis. Preliminary studies on the preparation of triazolines under chiral phase transfer catalysis are also presented, demonstrating that enantioenriched amides could be prepared from achiral aldehydes in moderate to low enantioselectivity.
Recommended Literature
- [1] An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile? Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo NamDalton Trans., 2016,45, 376-383 10.1039/C5DT04292E
- [2] An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes Adeline Huiling Loo,Alessandra Bonanni,Martin PumeraAnalyst, 2013,138, 467-471 10.1039/C2AN36199J
- [3] An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells? Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang ChengFood Funct., 2020,11, 10635-10644 10.1039/D0FO02131H
- [4] An ion-gating multinanochannel system based on a copper-responsive self-cleaving DNAzyme? Yang Chen,Di Zhou,Zheyi Meng,Jin ZhaiChem. Commun., 2016,52, 10020-10023 10.1039/C6CC03943J
- [5] An approach to biodegradable star polymeric architectures using disulfide coupling? Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. DavisChem. Commun., 2008, 6582-6584 10.1039/B817037A
- [6] Achieving high-efficiency purely organic room-temperature phosphorescence materials by boronic ester substitution of phenoxathiine? Mengke Li,Xinyi Cai,Zhenyang Qiao,Wentao Xie,Liangying Wang,Nan Zheng,Shi-Jian SuChem. Commun., 2019,55, 7215-7218 10.1039/C9CC02648G
- [7] An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders Jie Shen,Ying Zhou,Tu Lu,Junya Peng,Zhixiang Lin,Yuhong Pang,Li YuLab Chip, 2012,12, 317-324 10.1039/C1LC20845D
- [8] Aggregation dynamics, structure, and mechanical properties of bigels L. Di Michele,D. Fiocco,F. Varrato,E. Eiser,G. FoffiSoft Matter, 2014,10, 3633-3648 10.1039/C3SM52558A
- [9] An anti-leakage liquid metal thermal interface material Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng ChuRSC Adv., 2020,10, 18824-18829 10.1039/D0RA02351E
- [10] An approach for correlating the structural and electrical properties of Zr4+-modified SrBi4Ti4O15/SBT ceramic Priyambada Nayak,Tanmaya Badapanda,Anil Kumar Singh,Simanchalo PanigrahiRSC Adv., 2017,7, 16319-16331 10.1039/C7RA00366H
Journal Name:Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4