36201-07-7Relevant academic research and scientific papers
Pd-catalyzed imine-directed intramolecular C–N bond formation through C(sp3)–H activation: An efficient approach to multisubstituted pyrroles
Yu, Ting,Zhu, Qiang,Luo, Shuang
supporting information, (2020/04/08)
An atom-economic approach to synthesize 1,2,4-trisubstituted pyrroles through palladium-catalyzed imine-directed intramolecular C(sp3)–H amination reaction has been developed. The imine group acts as a directing group as well as an intramolecular nucleophile for the first time in intramolecular C–N bonds formation reactions.
Access to Cyclic β-Amino Acids by Amine-Catalyzed Enantioselective Addition of the γ-Carbon Atoms of α,β-Unsaturated Imines to Enals
Luo, Guoyong,Huang, Zhijian,Zhuo, Shitian,Mou, Chengli,Wu, Jian,Jin, Zhichao,Chi, Yonggui Robin
supporting information, p. 17189 - 17193 (2019/11/13)
Disclosed herein is a new catalytic approach for an efficient access to cyclic β-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ-carbon atoms of α,β-unsaturated imines to enals by iminium organic catalysis. This highly chemo- and stereo-selective reaction affords cyclic β-amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules.
Dynamic Kinetic Resolution of Allylic Azides via Asymmetric Dihydroxylation
Ott, Amy A.,Goshey, Charles S.,Topczewski, Joseph J.
supporting information, p. 7737 - 7740 (2017/06/21)
The catalytic enantioselective preparation of densely functionalized amines is a fundamental synthetic challenge. To address this challenge, we report for the first time that the Winstein rearrangement can be enlisted as the racemization pathway in a dynamic kinetic resolution of allylic azides. Alkene functionalization by Sharpless dihydroxylation affords tertiary azides in excellent enantioselectivity (up to 99:1 er). This approach establishes the chirality of the tertiary azide, obviates the need to directly forge either a congested C-N or C-C bond at the new nitrogenous stereocenter, and establishes additional functionality. Several examples demonstrate further elaboration of this functionality.
Synthesis and antimalarial activity of 3,3-spiroanellated 5,6-disubstituted 1,2,4-trioxanes
Maurya, Ranjani,Soni, Awakash,Anand, Devireddy,Ravi, Makthala,Raju, Kanumuri S.R.,Taneja, Isha,Naikade, Niraj K.,Puri,Wahajuddin,Kanojiya, Sanjeev,Yadav, Prem P.
supporting information, p. 165 - 169 (2013/03/29)
Novel 3,3-spiroanellated 5-aryl, 6-arylvinyl-substituted 1,2,4-trioxanes 19-34 have been synthesized and appraised for their antimalarial activity against multidrug-resistant Plasmodium yoelii nigeriensis in Swiss mice by oral route at doses ranging from 96 mg/kg × 4 days to 24 mg/kg × 4 days. The most active compound of the series (compound 25) provided 100% protection at 24 mg/kg × 4 days, and other 1,2,4-trioxanes 22, 26, 27, and 30 also showed promising activity. In this model, β-arteether provided 100 and 20% protection at 48 mg/kg × 4 days and 24 mg/kg × 4 days, respectively, by oral route. Compound 25 displayed a similar in vitro pharmacokinetic profile to that of reference drug β-arteether. The activity results demonstrated the importance of an aryl moiety at the C-5 position on the 1,2,4-trioxane pharmacophore.
