The use of boron chemistry for the synthesis of enantiomerically enriched organic compounds is described. Key advances towards the preparation of organoboranes with control of stereochemistry are supplemented by a discussion of the use of these chiral organoboranes in carbon-carbon bond forming reactions. Particular emphasis is given to advances in the Suzuki-Miyaura coupling of chiral secondary organoboranes and homologation reactions. Both of these reactions convert the initially generated B-C bond into a C-C bond and thus lead to a significant increase in complexity.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b911537dDOI Listing

Publication Analysis

Top Keywords

carbon-carbon bond
8
expanding scope
4
scope transformations
4
transformations organoboron
4
organoboron species
4
species carbon-carbon
4
bond
4
bond formation
4
formation retention
4
retention configuration
4

Similar Publications

The use of visible light to drive chemical transformations has a history spanning over a century. However, the development of photo-redox catalysts to efficiently harness light energy is a more recent advancement, evolving over the past two decades. While ruthenium and iridium-based photocatalysts dominate due to their photostability, long excited-state lifetimes, and high redox potentials, concerns about sustainability and cost have shifted attention to first-row transition metals.

View Article and Find Full Text PDF

BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues.

Biosensors (Basel)

December 2024

State Key Laboratory of Chemical Resource Engineering, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.

Peroxynitrite (ONOO) plays an important role in many physiological and pathological processes. Excessive ONOO in cells leads to oxidative stress and inflammation. However, precise monitoring of ONOO levels in specific organelles (e.

View Article and Find Full Text PDF

Zweifel olefination for C-glycosylation.

Commun Chem

December 2024

Technische Universität Darmstadt, Clemens-Schöpf-Institut für Organische Chemie und Biochemie, Peter-Grünberg-Straße 4, 64287, Darmstadt, Germany.

C-glycosides are significant in medicinal chemistry due to their resistance to enzymatic hydrolysis, making them more stable and bioavailable compared to O-glycosides. Their unique structure also offers potential for developing drugs with improved therapeutic properties, particularly in treating diseases like diabetes and cancer. The main challenge in synthesizing C-glycosides lies in forming the carbon-carbon bond between the sugar and aglycone efficiently, while controlling the stereochemistry and minimizing side reactions.

View Article and Find Full Text PDF

Catalytic Asymmetric Oxidative Coupling between C(sp)-H Bonds and Carboxylic Acids.

J Am Chem Soc

December 2024

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.

The direct enantioselective functionalization of C(sp)-H bonds in organic molecules could fundamentally transform the synthesis of chiral molecules. In particular, the enantioselective oxidation of these bonds would dramatically change the production methods of chiral alcohols and esters, which are prevalent in natural products, pharmaceuticals, and fine chemicals. Remarkable advances have been made in the enantioselective construction of carbon-carbon and carbon-nitrogen bonds through the C(sp)-H bond functionalization.

View Article and Find Full Text PDF

The cleavage of carbon-carbon bonds and their subsequent reassembly into highly functionalized and useful molecules in an atom-efficient manner has always been a central focus in the realm of organic synthesis. In this report, we describe the construction of highly functionalized naphthol esters via a tandem reassembly process, driven by Ullmann-type coupling of enaminones and 1,3-dicarbonyl compounds. Mechanistic investigations suggest the involvement of C(sp)-C(sp) coupling, cyclization, two acyl migrations, aromatization, and additional transformations within this tandem sequence.

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!