Nitrogen Heterocycle Synthesis through Hydride Abstraction of Acyclic Carbamates and Related Species: Scope, Mechanism, Stereoselectivity, and Product Conformation Studies.

Autor:	Miller JL; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, 15260, USA., Damodaran K; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, 15260, USA., Floreancig PE; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, 15260, USA.
Jazyk:	angličtina
Zdroj:	Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Dec 19; Vol. 29 (71), pp. e202302977. Date of Electronic Publication: 2023 Nov 05.
DOI:	10.1002/chem.202302977
Abstrakt:	Acyliminium ions and related species are potent electrophiles that can be quite valuable in the synthesis of nitrogen-containing molecules. This manuscript describes a protocol to form these intermediates through hydride abstractions of easily accessible allylic carbamates, amides, and sulfonamides that avoids the reversibility that is possible in classical condensation-based routes. These intermediates are used in the preparation of a range of nitrogen-containing heterocycles, and in many cases high levels of stereocontrol are observed. Specifically areas of investigation include the impact of chemical structure on oxidation efficiency, the geometry of the intermediate iminium ions, the impact of a substrate stereocenter on stereocontrol, and an examination of transition state geometry. (© 2023 Wiley-VCH GmbH.)
Databáze:	MEDLINE
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