Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles

Yedoyan, Julietta and Wurzer, Nikolai and Klimczak, Urszula and Ertl, Thomas and Reiser, Oliver (2019) Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 58 (11). pp. 3594-3598. ISSN 1433-7851, 1521-3773

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Abstract

A palladium-catalyzed coupling between aryl halides and monocyclopropanated pyrroles or furans has been developed, leading to valuable six-membered N- and O-heterocycles. As the key step, a selective cleavage of the non-activated endocyclic C-C bond of the 2-heterobicyclo-[3.1.0]hexane framework is achieved. The developed method offers access to highly functionalized piperidines, pyridines, and pyrans that are challenging to access by traditional methods.

Item Type: Article
Uncontrolled Keywords: DONOR-ACCEPTOR CYCLOPROPANES; DIELS-ALDER REACTIONS; ALDOL-TYPE REACTION; CARBONYL-COMPOUNDS; 2,2-DIALKOXYCYCLOPROPANECARBOXYLIC ESTERS; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; BUILDING-BLOCKS; ARYLATION; STRATEGY; 2H-pyrans; arylpyridines; dihydropyridines; donor-acceptor cyclopropanes; Heck coupling
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 21 Apr 2020 05:28
Last Modified: 21 Apr 2020 05:28
URI: https://pred.uni-regensburg.de/id/eprint/27373

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