Journal ArticleDOI
Cesium effect: high chemoselectivity in direct N-alkylation of amines
TLDR
The results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation, offering wide applications in peptidomimetic syntheses.Abstract:
A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.read more
Citations
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Journal ArticleDOI
Direct one-pot reductive N-alkylation of nitroarenes by using alcohols with supported gold catalysts.
TL;DR: It is reported for the first time that the simple Au/TiO2-VS system can catalyze the selective secondary or tertiary amine formation from the direct condensation of nitroarenes and alcohols in a valuable one-pot multistep transformation.
Journal ArticleDOI
Isolation of an N-alkylated Benzylamine Derivative from Pseudomonas putida BTP1 as Elicitor of Induced Systemic Resistance in Bean
Marc Ongena,Emmanuel Jourdan,Mathias Schäfer,Cécile Kech,Herbert Budzikiewicz,André Luxen,Philippe Thonart +6 more
TL;DR: Results indicate a wider variety of Pseudomonas determinants for ISR than reported to date, including the N-alkylated benzylamine derivative (NABD), which was first evidenced by testing the purified compound that mimicked the protective effect afforded by crude supernatant samples.
Journal ArticleDOI
Amination of Aliphatic Alcohols and Diols with an Iridium Pincer Catalyst
TL;DR: A number of transition metal-catalyzed reactions for the synthesis of aliphatic and aromatic amines, such as hydroamination of alkenes or alkynes 4] and aryl halides, has been developed as mentioned in this paper.
Patent
Sphingosine kinase inhibitors
TL;DR: In this paper substituted adamantane compounds, pharmaceutical compositions thereof, processes for their preparation, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease.
Journal ArticleDOI
Simultaneous solvent screening and reaction optimization in microliter slugs
TL;DR: An automated, continuous flow droplet screening system is presented, enabling real-time simultaneous solvent and continuous variable optimization of 1,2-diaminocyclohexane alkylation in 16 μL droplets, with scale-up demonstrated.
References
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Book
Reagents for Organic Synthesis
TL;DR: In this paper, the authors propose a method for using Reference Abbreviations (RABs) as a reference abbreviation for reference abbreviations in the context of bioinformatics.
Journal ArticleDOI
Synthesis of secondary amines
Journal ArticleDOI
An assessment of the causes of the cesium effect
TL;DR: In this paper, the effect of this effect on macrocyclization by means of nucleophilic substitution is discussed. But it is concluded that the cesium ion is virtually completely solvated and that carboxylates are essentially free and highly reactive.