Allylic amination, directly from alcohols, has been demonstrated without any Lewis acid activators using an efficient and regiospecific molecular iron catalyst. Various amines and alcohols were employed and the reaction proceeded through the oxidation/reduction (redox) pathway. A direct one-step synthesis of common drugs, such as cinnarizine and nafetifine, was exhibited from cinnamyl alcohol that produced water as side product.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201505214 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Rhodium-Catalyzed Allylic Amination for the Enantioselective Synthesis of Tertiary β-Fluoroamines.
Org Lett
January 2025
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, United States.
The utilization of β-fluoroamines as pharmaceutical components for drug development has attracted a considerable amount of interest. However, direct access to tertiary β-fluoroamines is challenging. We herein report the rhodium-catalyzed asymmetric amination of tertiary allylic trichloroacetimidates with anilines and cyclic aliphatic amines to access tertiary β-fluoroamines, where the α-carbon atom is bonded to four different substituents, in good yield with high levels of enantioselectivity.
View Article and Find Full Text PDFNickel Photoredox/Dual-Catalyzed Transfer Semi-Hydrogenation of Alkynes via Aminoalkyl Nickel Species.
J Org Chem
December 2024
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Using amines in catalytic transfer hydrogenation (TH) is challenging, despite their potential availability as a hydrogen source. Here, we describe a photoredox/nickel-catalyzed TH of alkyne through an intermediary aminoalkyl Ni species. This reaction successfully provided functionalized ()-alkenes, such as (homo)allyl ethers, alcohols, and amides (/ = up to >99:1), and the reaction thus bypasses a limitation of substrate scope in TH using amine and a Lindlar catalyst.
View Article and Find Full Text PDFFerrocenyl amines as directing groups for C-H activation have limitations as they are prone to undergo oxidation, allylic deamination, and β-hydride elimination. The fundamental challenge observed here is the competition between the desired C-H activation the vulnerable β-C-H bond activation of amines and fine-tuning of a suitable oxidant which avoids the oxidation of the β-C-H bond and ferrocene. Herein, the potential of an axially chiral NOBINAc ligand is revealed to implement the enantioselective Pd-catalyzed C-H activation process of ferrocenyl amines.
View Article and Find Full Text PDFAxially Chiral Phenanthroline Ligand-Enabled Pd-Catalyzed Asymmetric Amination and Alkylation of Aryl-Substituted Morita-Baylis-Hillman Adducts.
Org Lett
December 2024
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.
Highly enantioselective allylic amination and alkylation of racemic sterically hindered aryl-substituted Morita-Baylis-Hillman (MBH) adducts have been achieved by using an in situ formed Pd-catalyst from an axially chiral phenanthroline ligand. This dynamic kinetic asymmetric transformation (DYKAT) is compatible with cyclic and acyclic secondary amines, dialkyl malonates, β-keto esters, acetylacetone, and malononitrile, affording the corresponding chiral products, such as β-amino acid esters, in up to 95% yield and with up to a 99:1 enantiomeric ratio.
View Article and Find Full Text PDFSerotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-,-dimethyltryptamine Analogs in Mice.
ACS Chem Neurosci
December 2024
Designer Drug Research Unit, National Institute on Drug Abuse, Intramural Research Program, Baltimore, Maryland 21224, United States.
5-methoxy-,-dimethyltrytpamine (5-MeO-DMT) analogs are used as recreational drugs, but they are also being developed as potential medicines, warranting further investigation into their pharmacology. Here, we investigated the neuropharmacology of 5-MeO-DMT and several of its -alkyl, -allyl, and 2-methyl analogs, with three major aims: 1) to determine in vitro receptor profiles for the compounds, 2) to characterize in vitro functional activities at serotonin (5-HT) 2A receptors (5-HT) and 1A receptors (5-HT), and 3) to examine the influence of 5-HT on 5-HT-mediated psychedelic-like effects in the mouse head twitch response (HTR) model. In vitro receptor binding and functional assays showed that all 5-MeO-DMT analogs bind with high affinity and activate multiple targets (e.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!