Dual Catalysis Using Boronic Acid and Chiral Amine: Acyclic Quaternary Carbons via Enantioselective Alkylation of Branched Aldehydes with Allylic Alcohols.

J Am Chem Soc

Department of Chemistry, Centennial Centre for Interdisciplinary Science, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.

Published: August 2016

A ferrocenium boronic acid salt activates allylic alcohols to generate transient carbocations that react with in situ-generated chiral enamines from branched aldehydes. The optimized conditions afford the desired acyclic products embedding a methyl-aryl quaternary carbon center with up to 90% yield and 97:3 enantiomeric ratio, with only water as the byproduct. This noble-metal-free method complements alternative methods that are incompatible with carbon-halogen bonds and other sensitive functional groups.

Download full-text PDF

Source
http://dx.doi.org/10.1021/jacs.6b06101DOI Listing

Publication Analysis

Top Keywords

boronic acid
8
branched aldehydes
8
allylic alcohols
8
dual catalysis
4
catalysis boronic
4
acid chiral
4
chiral amine
4
amine acyclic
4
acyclic quaternary
4
quaternary carbons
4

Similar Publications

Toll-like receptor (TLRs) activation in multiple myeloma (MM) cells induces heterogeneous functional responses including cell growth and proliferation, survival or apoptosis. These effects have been suggested to be partly due to increase in secretion of cytokines such as IL-6 or IFNα among others from MM cells following TLR activation. However, whether triggering of these receptors also modulates production of immunoglobulin free light chains (FLCs), which largely contribute to MM pathology, has not been investigated in MM cells before.

View Article and Find Full Text PDF

Foremost in the design of new β-lactamase inhibitors (BLIs) are the boronic acid transition state inhibitors (BATSIs). Two highly potent BATSIs being developed are S02030 and MB076 strategically designed to be active against cephalosporinases and carbapenemases, especially KPC. When combined with cefepime, S02030 and MB076 demonstrated potent antimicrobial activity against laboratory and clinical strains of expressing a variety of class A and class C β-lactamases, including and .

View Article and Find Full Text PDF

Aromatic ring compounds with different conjugation degrees in a boronic acid matrix to realize multicolor phosphorescence for time division colorful multiplexing.

Nanoscale

January 2025

Electronic Materials Research Laboratory, Key Laboratory of the Ministry of Education International Center for Dielectric Research & Shaanxi Engineering Research Center of Advanced Energy Materials and Devices, Xi'an Jiaotong University, 710049 Xi'an, China.

Long lifetime multicolor phosphorescence materials possess excellent optical properties and have important application prospects in the fields of advanced anti-counterfeiting and information encryption. However, realizing long lifetime and color-tunable room temperature phosphorescent (RTP) carbon dot (CD) materials has proved challenging. In this study, the organic precursor molecules 2-phenethylamine (2-Ph), 9-aminophenanthrene (9-Ph) and 1-aminopyrene (1-Py) with different degrees of conjugation were selected to synthesize RTP CD composites: 2-Ph@BA, 9-Ph@BA and 1-Py@BA were synthesized by mixing with a boric acid (BA) matrix under high temperature pyrolysis.

View Article and Find Full Text PDF

Gelatin-Based Adhesive Hydrogels with Self-Healing, Injectable and Temperature-Triggered Detachable Properties.

Macromol Biosci

January 2025

School of Life Sciences and Health Engineering, Jiangnan University, Wuxi, Jiangsu, 214122, P. R. China.

Adhesive hydrogels are emerging as attractive functional materials for various fields, such as tissue engineering, wound healing, E-skins, etc. However, the removal of adhesive hydrogels from covered area may be painful and cause a secondary damage. In the current study, gelatin-based hydrogels are prepared by cross-linking with tannic acid and 4-formylphenyl boronic acid, through simultaneous dynamic covalent boronic ester and imine bond formations.

View Article and Find Full Text PDF

Cutaneous T-cell lymphoma (CTCL) is a rare T-cell malignancy characterized by inflamed and painful rash-like skin lesions that may affect large portions of the body's surface. Patients experience recurrent infections due to a compromised skin barrier and generalized immunodeficiency resulting from a dominant Th2 immune phenotype of CTCL cells. Given the role of the unfolded protein response (UPR) in normal and malignant T-cell development, we investigated the impact of UPR-inducing drugs on the viability, transcriptional networks, and Th2 phenotype of CTCL.

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!