A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched α-methylene-β-lactones.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5839468 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.7b00494 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photoredox-Catalyzed Alkene Acylesterification with Acyloxime Esters via C-C and Tertiary C-O Bond Formation.
Org Lett
January 2025
School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, Xi'an Jiaotong University, Xi'an 710049, China.
We describe an efficient acyl esterification method for alkenes utilizing acyloxime esters as bifunctional reagents featuring radical acylation and congested C-O bond formation. This approach is characterized by mild photoredox conditions, high step and atom economy, a broad substrate scope, and excellent regioselectivity. A variety of valuable α-acyl hindered alcohol esters, including those obtained via gram-scale synthesis and late-stage functionalization of pharmaceutical molecules, were presented, demonstrating its synthetic potential and practicability.
View Article and Find Full Text PDFThe acyl-CoA-binding protein VdAcb1 is essential for carbon starvation response and contributes to virulence in .
aBIOTECH
December 2024
State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing, 100193 China.
Unlabelled: In the face of carbon, nitrogen, and phosphorus starvation, microorganisms have evolved adaptive mechanisms to maintain growth. In a previous study, we identified a protein predicted to contain acyl-CoA-binding domains in the plant pathogenic fungus . The predicted protein, designated VdAcb1, possesses an atypical signal peptide.
View Article and Find Full Text PDFEffect of Triterpenoids Betulin and Betulinic Acid on Pulmonary Surfactant Membranes.
J Membr Biol
December 2024
Faculty of Science, Department of Physics, Ege University, 35100, Bornova, Izmir, Turkey.
Article Synopsis
- - The study investigates how triterpenoids betulin (BE) and betulinic acid (BA) influence the behavior and packing of pulmonary surfactant membranes, particularly focusing on their effects on dipalmitoylphosphatidylcholine (DPPC) bilayers using various scientific methods.
- - Findings indicate that BE has a more significant impact on DPPC than BA; BE at 20 mol% causes changes in phase transitions, while BA at lower concentrations decreases the main transition temperature and disrupts the pretransition entirely.
- - Both triterpenoids enhance lateral mobility and dehydration in DPPC structures, leading to larger liposomes and changed molecular interactions, demonstrated by hydrogen bonding between the triterpenoids and
A Rare Case of Magnesium Alkyl Mediated CO-to-Alkoxide Conversion.
Chemistry
November 2024
Inorganic and Organometallic Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 1, 91058, Erlangen, Germany.
Alcohols can be produced by nucleophilic addition at the C=O functional group of ketones or aldehydes. Such C-C bond formations generally proceed smoothly and selective. In contrast, nucleophilic addition at carbon monoxide is considerably more complex and unselective due to the instability of polar metal acyl intermediates.
View Article and Find Full Text PDFPauli Exclusion by n→π* Interactions: Implications for Paleobiology.
ACS Cent Sci
October 2024
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Proteins have evolved to function in an aqueous environment. Collagen, which provides the bodily scaffold for animals, has a special need to retain its integrity. This need was addressed early on, as intact collagen has been detected in dinosaur fossils, even though peptide bonds have a half-life of only ∼500 years in a neutral aqueous solution.
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!