An unprecedented intramolecular Petasis condensation provides a novel approach to biologically important conduramines. The compounds are produced with an exclusive anti stereoselectivity for the newly created β-amino alcohol motif. The stereochemical outcome of the reaction is opposite to the one usually observed in the intermolecular reaction.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol203162sDOI Listing

Publication Analysis

Top Keywords

remarkable stereoselectivity
4
stereoselectivity intramolecular
4
intramolecular borono-mannich
4
borono-mannich reactions
4
reactions synthesis
4
synthesis conduramines
4
conduramines unprecedented
4
unprecedented intramolecular
4
intramolecular petasis
4
petasis condensation
4

Similar Publications

A Hexavalent Tellurium-Based Chalcogen Bonding Catalysis Platform: High Catalytic Activity and Controlling of Selectivity.

J Am Chem Soc

January 2025

School of Chemistry and Chemical Engineering, Key Laboratory of Colloid and Interface Chemistry of the Ministry of Education, Shandong University, Jinan 250100, P. R. China.

Herein, we describe a hexavalent tellurium-based chalcogen bonding catalysis platform capable of addressing reactivity and selectivity issues. This research demonstrates that hexavalent tellurium salts can serve as a class of highly active chalcogen bonding catalysts for the first time. The tellurium centers in these hexavalent catalysts have only one exposed interaction site, thus providing a favorable condition for the controlling of reaction selectivity.

View Article and Find Full Text PDF

Protein Engineering of Substrate Specificity toward Nitrilases: Strategies and Challenges.

J Agric Food Chem

January 2025

Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Life Sciences and Health Engineering, Jiangnan University, Wuxi 214122, PR China.

Nitrilase is extensively applied across diverse sectors owing to its unique catalytic properties. Nevertheless, in industrial production, nitrilases often face issues such as low catalytic efficiency, limited substrate range, suboptimal selectivity, and side reaction products, which have garnered heightened attention. With the widespread recognition that the structure of enzymes has a direct impact on their catalytic properties, an increasing number of researchers are beginning to optimize the functional characteristics of nitrilases by modifying their structures, in order to meet specific industrial or biotechnology application needs.

View Article and Find Full Text PDF

Background: Indoxacarb, a type of chiral pesticide, is used to control Lepidoptera insects. Most studies had focused on the environmental behavior and selective toxicity of indoxacarb enantiomers, and the mechanism behind its selective biological activity against target organisms is not well understood.

Results: Spodoptera frugiperda was selected as the target insect.

View Article and Find Full Text PDF

This study examined the chemoselectivity and diastereoselectivity of silyl nitronate alkenyn-nitroethers in Intramolecular Silyl Nitronate Cycloadditions (ISNCs) to produce isoxazole derivatives with interesting medicinal properties. These reactions resulted in the formation of either dihydrofuro[3,4-c]isoxazolines/isoxazolidines and/or alkynyl moieties attached to 2,5-dihydrofuryl carbonyls. This study also discerned the diastereoselectivities of the resulting cyclic adducts and compared them to previous findings.

View Article and Find Full Text PDF

Aromatic ring-opening metathesis.

Nature

December 2024

Department of Chemistry, University of Basel, Basel, Switzerland.

Aromatic compounds are used across chemistry and materials science as a result of their stability, characteristic interactions, defined molecular shape and the numerous synthetic approaches for their synthesis by a diversity of cyclization reactions. In contrast, the cleavage of inert aromatic carbon-carbon bonds remained largely unfeasible due to the unfavourable energetics of disrupting aromaticity on ring opening. For non-aromatic structures, alkene metathesis catalysed by transition metal alkylidenes is established as one of the most versatile carbon-carbon bond-forming and breaking reactions.

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!