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Chemistry. 2013 Apr 2;19(14):4414-8. doi: 10.1002/chem.201300030. Epub 2013 Feb 27.

Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.

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  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125, USA.

Abstract

Eeny, meeny, miny ... enaminones! Lactams and imides have been shown to consistently provide enantioselectivities substantially higher than other substrate classes previously investigated in the palladium-catalyzed asymmetric decarboxylative allylic alkylation. Several new substrates have been designed to probe the contributions of electronic, steric, and stereoelectronic factors that distinguish the lactam/imide series as superior alkylation substrates (see scheme). These studies culminated in marked improvements on carbocyclic allylic alkylation substrates.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PMID:
23447555
[PubMed - indexed for MEDLINE]
PMCID:
PMC3815597
Free PMC Article
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