Enantioselective N-heterocyclic carbene-catalyzed Michael addition to α,β-unsaturated aldehydes by redox oxidation.

Org Lett

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

Published: August 2011

Enantioselective N-heterocyclic carbene-catalyzed Michael addition reactions to α,β-unsaturated aldehydes by redox oxidation were realized. With 10 mol % of camphor-derived triazolium salt D, 15 mol % of DBU, 5 mol % of NaBF(4), and 100 mol % of quinone oxidant, the reactions of various dicarbonyl compounds with α,β-unsaturated aldehydes led to 3,4-dihydro-α-pyrones in good yields and excellent ee's.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol201595fDOI Listing

Publication Analysis

Top Keywords

αβ-unsaturated aldehydes
12
enantioselective n-heterocyclic
8
n-heterocyclic carbene-catalyzed
8
carbene-catalyzed michael
8
michael addition
8
aldehydes redox
8
redox oxidation
8
addition αβ-unsaturated
4
oxidation enantioselective
4
addition reactions
4

Similar Publications

Background: Tubular injury triggered by hyperglycemia is an important pathological characteristic in diabetic nephropathy (DN). Accumulated advanced glycation end products and their precursor methylglyoxal (MGO), contribute to the development of DN. Carnosine has been shown to prevent the development of DN but the underlying mechanism still needs to be studied in depth.

View Article and Find Full Text PDF

Elucidating the Phase I metabolism of psilocin in vitro.

Arch Toxicol

January 2025

Department of Pharmacy and Pharmaceutical Sciences, National University of Singapore, 18 Science Drive 4, Singapore, 117543, Singapore.

Psilocin is a well-studied controlled substance with potential psychotherapeutic applications. However, research gaps remain regarding its metabolism. Our objective was to elucidate a comprehensive Phase I metabolic profile of psilocin to support its forensic management and clinical development.

View Article and Find Full Text PDF

Background: Numerous studies have highlighted the role of oxidative stress in Alzheimer's disease (AD) development. Yet, the alignment of systemic and central oxidative stress biomarkers is unclear across diverse populations in the AD continuum. This study aims to assess protein damage levels in plasma and cerebrospinal fluid (CSF) within the AD continuum.

View Article and Find Full Text PDF

Basic Science and Pathogenesis.

Alzheimers Dement

December 2024

Center of Excellence in Cardiac Electrophysiology Research, Chiang Mai University, Chiang Mai, Thailand.

Background: Our previous studies reported that D-galactose (D-gal) administration for four to eight weeks caused metabolic disturbance, brain mitochondrial dysfunction, and brain aging, leading to cognitive dysfunction in similar with natural aging condition. Spermidine is a polyamine that can be found naturally. Spermidine has been showed the beneficial effects on various models, such as attenuating metabolic/gut impairments in obesity, and ameliorating memory loss in aged model.

View Article and Find Full Text PDF

We report the application of organoiridium complexes as catalytic agents for the detoxification of biogenic reactive aldehyde species (RASP), which are implicated in the pathogenesis of neurodegenerative disorders. We show that Ir complexes functionalized with phosphonium cations localize selectively in the mitochondria and have better cellular retention compared to that of their parent Ir species. In a cell model for Parkinsonism, the mitochondria-targeted iridium catalysts exhibited superior cell protecting abilities and longer-lasting effects (up to 6 d) than conventional RASP scavengers, which failed to be effective beyond 24 h.

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!