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
Elucidation of Structural Elements for Selectivity across Monoamine Transporters: Novel 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues
Oluyomi M. Okunola-Bakare,Jianjing Cao,Theresa A. Kopajtic,Jonathan L. Katz,Claus J. Loland,Lei Shi,Amy Hauck Newman +6 more
TL;DR: Molecular docking studies, using a subset of analogues with DAT and SERT homology models, and functional data obtained defined a role for TM10 in the substrate/inhibitor S1 binding sites of DATand SERT.
Journal ArticleDOI
Monoalkylation of primary amines and N-sulfinylamides
TL;DR: An efficient monoalkylation of primary amines with primary or secondary alcohols catalyzed by Ra-Ni under mild conditions is described.
Journal ArticleDOI
Clean synthesis of primary to tertiary carboxamides by CsOH-catalyzed aminolysis of nitriles in water
TL;DR: In this article, a clean synthesis of a wide range of primary, secondary, and tertiary carboxamides was achieved by aminolysis reactions of nitriles with ammonia, primary, or secondary amines in water.
Journal ArticleDOI
Highly selective N-Alkylation of amines promoted on silica: An efficient and recyclable surface
TL;DR: In this article, the authors studied N-alkylation of amines with various types of alkyl halides, which finally constitute practical, highly selective and eco-friendly conditions for mono- or bisalkylated amines at ambient temperature with recyclability of silica.
Journal ArticleDOI
Ruthenium‐Catalyzed Transfer Hydrogenation of Nitriles: Reduction and Subsequent N‐Monoalkylation to Secondary Amines
TL;DR: In this paper, a domino ruthenium-catalyzed transfer hydrogenation of nitriles with subsequent N-monoalkylation by using alcohols is described.
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
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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.