Role of quaternary ammonium salts as new additives in the enantioselective organocatalytic β-benzylation of enalsThis article is part of the joint ChemComm-Organic & Biomolecular Chemistry 'Organocatalysis' web themed issue.Electronic supplementary information (ESI) available: Experimental and computational details, spectra, and chiral HPLC conditions. See DOI: 10.1039/c2cc31451g

We report herein the efficiency of quaternary ammonium salts as co-catalysts in organocatalytic Michael reactions involving iminium activation of α,β-unsaturated aldehydes. The enantioselective formal benzylation of these substrates has been optimized and used to rationalize the role of the ammonium...

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Main Authors: Duce, Sara, Mateo, Alvaro, Alonso, Inés, García Ruano, José Luis, Cid, M. Belén
Format: Article
Language:English
Online Access:Get full text
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Summary:We report herein the efficiency of quaternary ammonium salts as co-catalysts in organocatalytic Michael reactions involving iminium activation of α,β-unsaturated aldehydes. The enantioselective formal benzylation of these substrates has been optimized and used to rationalize the role of the ammonium salts in these processes. Quaternary ammonium salts act as efficient neutral additives in organocatalyzed Michael additions to enals, promoting sequential iminium-enolate formation.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc31451g