[reaction: see text] A diastereomeric mixture of the alpha-amino nitrile prepared by the Strecker reaction of benzaldehyde, (1S,2R)-1-aminoindan-2-ol, and cyanotrimethylsilane thermally epimerizes in the solid state to give a single diastereomer with an (S)-configuration at the alpha position to the nitrile moiety. This shows a sharp contrast to the reaction conducted in DMSO at room temperature, which gives a 1:1 mixture of (S)- and (R)-isomers. Several other alpha-amino nitriles also epimerize in the solid-state toward single diastereomers.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol049256q | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Perampanel reduces seizure frequency in patients with developmental and epileptic encephalopathy for a long term.
Sci Rep
December 2024
Department of Pediatrics, Jichi Medical University, 3311-1 Yakushiji, Shimotsuke City, Tochigi, 329-0498, Japan.
Seizures in patients with developmental and epileptic encephalopathies (DEEs) are often highly resistant to various antiseizure medications. Perampanel (PER) is a novel antiseizure medication that non-competitively inhibits the α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor and is expected to reduce seizure frequency not only for focal seizures and generalized tonic-clonic seizures (GTCS) but also for other seizure types. This study aimed to clarify the long-term therapeutic efficacy and tolerability of PER in patients with DEEs.
View Article and Find Full Text PDFNickel-Catalyzed Difluoroalkylation of β,γ-Unsaturated α-Amino Nitrile Derived Lithium Reagents.
Angew Chem Int Ed Engl
November 2024
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, 200032, Shanghai, China.
Organolithium reagents, known for their low cost, ready availability, and high reactivity, allow fast cross-coupling under ambient conditions. However, their direct cross-coupling with fluoroalkyl electrophiles remains a formidable challenge due to the easy formation of thermo-unstable fluoroalkyl lithium species during the reaction, which are prone to decomposition via rapid α/β-fluoride elimination. Here, we exploit heteroatom-stabilized allylic anions to harness the exceptional reactivity of organolithium reagents, enabling the compatibility of difluoroalkyl halides and facilitating versatile and precise fluorine functionality introduction under mild conditions.
View Article and Find Full Text PDFEnantioselective Deoxygenative Amino-Cyanation of Carboxylic Acids via Ti-Multicatalysis.
Org Lett
November 2024
Department of Chemistry, Clemson University, Clemson, South Carolina 29634, United States.
Carboxylic acids are valued synthetic building blocks that offer shelf life stability, structural diversity, and wide commercial availability. Despite the remarkable synthetic utility of carboxylic acids, a direct enantioselective deoxygenative functionalization of carboxylic acids remains rare. We present enantioselective deoxygenative amino-cyanation of carboxylic acids using a novel Ti-multicatalytic system that catalytically modified each C-O bond of carboxylic acid to C-C, C-N, and C-H bonds, generating enantio-enriched chiral α-amino nitriles (up to 98:2 er).
View Article and Find Full Text PDFRole of α-amino-3‑hydroxy-5-methyl-4-isoxazolepropionic acid receptors and the antagonist perampanel in geriatric epilepsy and status epilepticus.
Arch Gerontol Geriatr
January 2025
Department of Neurology, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, 138 Sheng-Li Rd, Tainan 70428, Taiwan. Electronic address:
The α-amino-3‑hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) is an ionotropic glutamate receptor recognized for its active involvement in epilepsy. Through AMPAR functional alterations, multiple factors contribute to the increased susceptibility to seizures in the geriatric population. These factors include changes in the hippocampus, neuroinflammation, ischemic insults, amyloid deposition, previous seizures, alterations in the microenvironment, and neurovascular unit dysfunction.
View Article and Find Full Text PDFEfficient synthesis of α-amino-vinylphosphine oxides from alkyl nitriles manganese-catalyzed phosphinoenamination.
Org Biomol Chem
June 2024
Department of Chemistry, Nanchang University, Xuefu Rd. 999, Nanchang, 330031, P. R. China.
A protocol for the synthesis of α-amino-vinylphosphine oxides by phosphinoenamination reaction between alkyl nitriles and phosphine oxides was developed. The combination of Mn(OAc) as a Lewis acid and guanidine as a Lewis base was found to be an efficient catalytic system for this reaction. A series of alkyl nitriles and phosphine oxides are compatible with this conversion, furnishing the desired products in up to 95% yield under mild conditions.
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!