Activity and selectivity of DMAP derivatives in acylation reactions.pdf

Activity and selectivity of DMAP derivatives in acylation reactions

Evgeny Larionov

The main topic of this book is application of theoretical and experimental methods for the development of acylation catalysts based on the DMAP (4-dimethylaminopyridine) motif. The usefulness of the computational approach is demonstrated using examples from stereoselective catalysis (where the conformational properties of intermediates are relevant) and from the development of more active catalysts (where the relative stabilities of intermediates are relevant). First, a theoretical and experimental study of the structure-reactivity relationship of alcohol acetylation catalyzed by pyridine derivatives has been performed. The ground state model has then been applied to the computational design of photoswitchable pyridines as well as planar-chiral aminopyridine derivatives, containing paracyclophane or ferrocenyl substituents. Design of a new class of acylation catalysts, which combine pyridine as a nucleophilic part and a (thio)urea fragment as hydrogen bonding moiety, is also described in this book. Finally, some mechanistic insights into the catalytic system for the kinetic resolution, both experimental and theoretical, are described in the last chapter.

Carbonylimidazole derivatives are highly active acylation reagents for esterification and amidation in the presence of pyridinium salts as catalysts. These reactions are thought to involve both Brønsted acid and nucleophilic catalysis. This mode of activation has been applied to the synthesis of difficult to access oxazolidinones, as well as

9783838127675 ISBN
Activity and selectivity of DMAP derivatives in acylation reactions.pdf


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Pergamon Tetrahedron Letters 39 (1998) 8919-8922 TETRAHEDRON LETTERS Synthesis of Atropisomeric Analogues of DMAP Alan C. Spivey1., Tomasz Fekner, and Harry Adams Department ~ff'Chemistrv, University of Sheffield, Brook Hill. Investigation of the Carboxylate Position during …

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4-Dimethylaminopyridine - Wikipedia 4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH 3) 2 NC 5 H 4 N. This colourless solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe 2 substituent.. Because of its basicity, DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis

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