Copper triflate-BOX complexes catalyse the enantioselective conjugate addition of methyl malonate to β-trifluoromethyl-α,β-unsaturated imines to give the corresponding enamines bearing a trifluoromethylated stereogenic centre with good yields, and diastereo- and enantioselectivities. The usefulness of the method has been shown with the synthesis of optically active β-trifluoromethyl δ-amino esters and optically active trifluoromethyl piperidones.
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http://dx.doi.org/10.1039/c7ob00595d | DOI Listing |
J Org Chem
January 2025
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, India.
We have developed efficacious routes toward the selective synthesis of two classes of compounds such as C-3 amino-methylated indoles and 4-indol-3-yl-methylanilines from the same precursors, namely, indoles and 1,3,5-triazinanes. It is reported that the controlled cleavage of 1,3,5-triazinanes can be effected by heat for the generation of aryl imine motifs, and we observed that the presence of Lewis acid influences the course of these transformations toward different products. The reaction toward indol-3-yl-methylanilines proceeds via a nucleophilic attack of indole to the aryl imine generated from the 1,3,5-triazinanes to form an amino-methylated product which undergoes a Lewis acid mediated Hofmann-Martius-type rearrangement.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.
The reactivity between sulfonimidamide-derived imines and cyclic anhydrides has been investigated. Sulfonimidamide imines readily react with homophthalic anhydride under mild conditions in the presence of non-nucleophilic bases to yield complex lactam products with high diastereoselectivity. Furthermore, it was discovered that sulfonimidamide imines react with homophthalic anhydride in the absence of a base to yield distinct diastereomer products with high diastereoselectivity.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Sun Yat-Sen University, School of Material Science and Engineering, Nr.135 Xingang Xi Road, 510275, Guangzhou, CHINA.
Degradable features are highly desirable to advance next-generation organic mixed ionic-electronic conductors (OMIECs) for transient bioinspired artificial intelligence devices.It is highly challenging that OMIECs exhibit excellent mixed ionic-electronic behavior and show degradability simultaneously.Specially,in OMIECs,doping is often a tradeoff between structural disorder and charge carrier mobilities.
View Article and Find Full Text PDFNat Chem
January 2025
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, China.
The substitution of an aromatic ring with a C(sp)-rich bicyclic hydrocarbon, known as bioisosteric replacement, plays a crucial role in modern drug discovery. Substituted bicyclo[1.1.
View Article and Find Full Text PDFNat Commun
January 2025
School of Energy and Environment, Southeast University, Nanjing, Jiangsu, 210096, P. R. China.
As bacterial contamination crises escalate, the development of advanced membranes possessing both high flux and antibacterial properties is of paramount significance for enhancing water sterilization efficiency. Herein, an ultrathin layer of TbPa (an imine-linked covalent organic framework) and nanosized CuO clusters, sequentially deposited onto polyethersulfone membranes, demonstrate exceptional water flux performance, reaching a permeance level of 16000 LHM bar. The deposited TbPa, generating uniformly distributed reduction sites under illumination, facilitates the uniform formation of CuO clusters.
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