A Cross-Metathesis/Aza-Michael Reaction Strategy for the Synthesis of Cyclic and Bicyclic Ureas.

J Org Chem

Department of Chemistry , University of Michigan , 930 North University Avenue, Ann Arbor , Michigan 48109-1055 , United States.

Published: September 2018

The synthesis of cyclic and bicyclic ureas via a ruthenium-catalyzed cross-metathesis / aza-Michael reaction strategy between protected alkenyl ureas and Michael acceptors is described. The substrates for these reactions are generated in 1-3 steps from commercially available materials, and products are formed in moderate yield with up to >20:1 diastereoselectivity.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.8b01492DOI Listing

Publication Analysis

Top Keywords

reaction strategy
8
synthesis cyclic
8
cyclic bicyclic
8
bicyclic ureas
8
cross-metathesis/aza-michael reaction
4
strategy synthesis
4
ureas synthesis
4
ureas ruthenium-catalyzed
4
ruthenium-catalyzed cross-metathesis / aza-michael
4
cross-metathesis / aza-michael reaction
4

Similar Publications

Radical covalent organic frameworks (RCOFs) have demonstrated significant potential in redox catalysis and energy conversion applications. However, the synthesis of stable RCOFs with well-defined neutral carbon radical centers is challenging due to the inherent radical instability, limited synthetic methods and characterization difficulties. Building upon the understanding of stable carbon radicals and structural modulations for preparing crystalline COFs, herein we report the synthesis of a crystalline carbon-centered RCOF through a facile post-oxidation process.

View Article and Find Full Text PDF

Photocatalytic Direct Borylation of Benzothiazole Heterocycles via a Triplet Activation Strategy.

Org Lett

January 2025

Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, China.

Boron compounds are widely employed in organic chemistry, pharmaceuticals, and materials science. Among them, borylated heterocycles serve as versatile synthons for the construction of new C-C or C-heteroatom bonds via coupling or radical processes. Such methods for direct C-H borylation reactions are of high synthetic value to reduce the number of synthetic steps and the amount of waste and to improve efficiency.

View Article and Find Full Text PDF

Transition-metal dichalcogenides (TMDs), such as molybdenum disulfide (MoS), have emerged as a generation of nonprecious catalysts for the hydrogen evolution reaction (HER), largely due to their theoretical hydrogen adsorption energy close to that of platinum. However, efforts to activate the basal planes of TMDs have primarily centered around strategies such as introducing numerous atomic vacancies, creating vacancy-heteroatom complexes, or applying significant strain, especially for acidic media. These approaches, while potentially effective, present substantial challenges in practical large-scale deployment.

View Article and Find Full Text PDF

Debus-Radziszewski Reaction Inspired In Situ "One-Pot" Approach to Construct Luminescent Zirconium-Organic Frameworks.

Inorg Chem

January 2025

Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic University, 7098 Liuxian Blvd, Nanshan District, Shenzhen 518055, P. R. China.

Metal-organic frameworks have received extensive development in the past three decades, which are generally constructed via the reaction between inorganic building units and commercially available or presynthesized organic linkers. However, the presynthesis of organic linkers is usually time-consuming and unsustainable due to multiple-step separation and purification. Therefore, methodology development of a new strategy is fundamentally important for the construction and further exploration of the applications of MOFs.

View Article and Find Full Text PDF

Despite tremendous progress of dienamine catalysis along with its application in enantioselective synthesis over nearly two decades, certain limitations, especially with respect to the regioselectivity in the dienamine generation step, continue to persist. To overcome these shortcomings of classical dienamine catalysis, we now introduce the concept of alkoxy-directed dienamine catalysis and apply it to the enantioselective arene construction by desymmetrizing -enediones through [4 + 2]-cycloaddition. Catalyzed by a diphenylprolinol silyl ether, this reaction utilizes γ-alkoxy α,β-unsaturated aldehydes as the substrate and proceeds in a highly regioselective fashion through the intermediacy of δ-alkoxy dienamine.

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!