Editorial pubs.acs.org/OPRD
Invited Review
I
t is with pleasure that we introduce an invited contribution from Professor Jonathan Ellman from Yale University featuring synthetic approaches to tetrahydropyridines utilizing Rh(I)-catalyzed C−H functionalization. Functionalized piperidines and dihydropiperidines are common motifs in pharmaceutical drug candidates and natural products. Their syntheses often arise from derivatization of pyridines which have limited substitution patterns or require multistep synthesis. The Ellman group has recently developed synthetic methodology where an α,β-unsaturated imine is used in a rhodium-catalyzed alkenylation/electrocyclization sequence to efficiently produce a dihydropyridine that can be further elaborated through reaction with a nucleophile or cycloaddition with an alkene or alkyne. In a second contribution, exemplification of the methodology was conducted on a 20 g scale in high yield requiring only 0.25 mol % of the appropriate catalyst. The synthetic method presented provides a rapid entry to highly functionalized tetrahydropyridines with excellent relative stereocontrol. We hope that these publications will lead to increased applications of this powerful method in both academic and industrial laboratories. We thank Professor Ellman for his contribution to OPRD.
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Steṕ hane Caron*
AUTHOR INFORMATION
Corresponding Author
*E-mail: stephane.caron@pfizer.com. Notes
Views expressed in this editorial are those of the author and not necessarily the views of the ACS.
Published: August 29, 2014 © 2014 American Chemical Society
1096
dx.doi.org/10.1021/op500238t | Org. Process Res. Dev. 2014, 18, 1096−1096
