CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.

Org Lett

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Published: July 2020

The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8027949PMC
http://dx.doi.org/10.1021/acs.orglett.0c02064DOI Listing

Publication Analysis

Top Keywords

carboxylic acids
12
αβ-unsaturated carboxylic
8
cuh-catalyzed asymmetric
4
asymmetric reductive
4
reductive amidation
4
amidation αβ-unsaturated
4
acids direct
4
direct enantioselective
4
enantioselective copper
4
copper hydride
4

Similar Publications

Child Neurology: Severe -Related Congenital Muscular Dystrophy With Rapidly Progressive Encephalopathy Leading to Infantile Death.

Neurology

February 2025

Division of Clinical and Metabolic Genetics, Department of Paediatrics, The Hospital for Sick Children, University of Toronto, Ontario, Canada.

Pathogenic variants in cause congenital muscular dystrophy through hypoglycosylation of alpha-dystroglycan (OMIM #615350). The established phenotypic spectrum of GMPPB-related disorders includes recurrent rhabdomyolysis, limb-girdle muscular dystrophy, neuromuscular transmission abnormalities, and congenital muscular dystrophy with variable brain and eye anomalies. We report a 9-month-old male infant with congenital muscular dystrophy, infantile spasms, and compound heterozygous pathogenic variants (c.

View Article and Find Full Text PDF

Inhibitory Effect on the Tyrosinase Activity and Low Cytotoxicity of Monounsaturated Long-Chain Chelating Fatty Ester.

An Acad Bras Cienc

January 2025

Universidade Federal do Pará, Instituto de Ciências Exatas e Naturais, Laboratório de Investigação Sistemática em Biotecnologia e Biodiversidade Molecular, Rua Augusto Corrêa, 01, 66075-110 Belém, PA, Brazil.

In the present study, 5-Hydroxy-2-(Oleoyloxymethyl) -4H-pyran-4-one (KMO 3), and their chelated with Cu(II) and Fe(III) ions were synthesized to explore their inhibitory activity against tyrosinase and cytotoxicity. To this end, the structures of the obtained compounds were confirmed by ATR/FT-IR, 13C and 1H-NMR, and UV-vis techniques. The results show that chelating fatty ester presents the bands at 1567m, 1511w cm-1 attributed to the coordinated carbonyl (Cu(II)←[O=C]2), and the bands at 1540m, 1519m cm-1 which were attributed to the coordinated carbonyl (Fe(III)←[O=C]3).

View Article and Find Full Text PDF

Purpose: We aimed to investigate the role of gallic acid treatment on spinal cord tissues after spinal cord injury (SCI) and its relationship with endoplasmic reticulum (ER) stress by histochemical, immunohistochemical, and in-silico techniques.

Methods: Thirty female Wistar albino rats were divided into three groups: sham, SCI, and SCI+gallic acid. SCI was induced by dropping a 15-g weight onto the exposed T10-T11 spinal cord segment.

View Article and Find Full Text PDF

Bedaquiline, pretomanid, linezolid, and moxifloxacin (BPaLM) for multidrug- or rifampin-resistant tuberculosis: a systematic review.

J Bras Pneumol

January 2025

. Instituto de Doenças do Tórax - IDT - Faculdade de Medicina, Universidade Federal do Rio de Janeiro - UFRJ - Rio de Janeiro (RJ) Brasil.

Objective: To evaluate the available evidence comparing the use of the bedaquiline, pretomanid, linezolid, and moxifloxacin (BPaLM) regimen for 6 months with that of standard-of-care regimens for patients with multidrug-resistant or rifampin-resistant tuberculosis (MDR/RR-TB).

Methods: This was a systematic review of clinical trials comparing the use of the BPaLM regimen with the standard of care in patients with MDR/RR-TB. The main outcome measure was an unfavorable endpoint (a composite of death, treatment failure, treatment discontinuation, loss to follow-up, and recurrence), and secondary outcome measures included adverse events and serious adverse events.

View Article and Find Full Text PDF

Interaction between saflufenacil and ammonium glufosinate to control ryegrass.

Braz J Biol

January 2025

Universidade Federal de Santa Maria - UFSM, Departamento de Defesa Fitossanitária, Santa Maria, RS, Brasil.

Annual ryegrass (Lolium multiflorum Lam.) is one of the main weeds in subtropical cropping systems of Europe, Oceania and South America. Therefore, the hypothesis of this work is that the interaction between ammonium glufosinate and saflufenacil can be synergistic for ryegrass control.

View Article and Find Full Text PDF

Want 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!