3 years ago

An Aminocatalyzed Michael Addition/Iron-Mediated Decarboxylative Cyclization Sequence for the Preparation of 2,3,4,6-Tetrasubstituted Pyridines: Scope and Mechanistic Insights

An Aminocatalyzed Michael Addition/Iron-Mediated Decarboxylative Cyclization Sequence for the Preparation of 2,3,4,6-Tetrasubstituted Pyridines: Scope and Mechanistic Insights
Igor D. Jurberg, Mateus L. Stivanin, Marcelo Duarte, Naylil M. R. Capreti, Celio F. F. Angolini, Camila Sartori
A novel, scalable strategy for the preparation of 2,3,4,6-tetrasubstituted pyridines is described. This protocol has two steps: an aminocatalyzed addition of ketones to alkylidene isoxazol-5-ones, followed by an iron-mediated decarboxylative cyclization event. Mechanistic insights for both steps are provided based on HRMS-ESI(+) studies.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01789

DOI: 10.1021/acs.joc.7b01789

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