A Pd-Catalyzed Synthesis of Functionalized Piperidines

Benjamin D W Allen; Matthew J Connolly; Joseph P A Harrity

doi:10.1002/chem.201602586

A Pd-Catalyzed Synthesis of Functionalized Piperidines

Chemistry. 2016 Sep 5;22(37):13000-3. doi: 10.1002/chem.201602586. Epub 2016 Jul 5.

Authors

Benjamin D W Allen¹, Matthew J Connolly¹, Joseph P A Harrity²

Affiliations

¹ Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, U.K.
² Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, U.K.. j.harrity@sheffield.ac.uk.

PMID: 27273202
DOI: 10.1002/chem.201602586

Abstract

A readily available cyclic carbamate 1 functions as a general precursor to a range of functionalized piperidine products via a new Pd-catalyzed annulation strategy. An asymmetric catalytic variant provides a rapid and efficient means to access these heterocycles with high to excellent levels of enantiocontrol. Finally, these richly functionalized compounds are amenable to further chemoselective elaboration.

Keywords: Pd catalysis; annulation; enantioselectivity; piperidine.