Oxidation of allylic and benzylic alcohols to aldehydes and carboxylic acids

An oxidation of allylic and benzylic alcohols to the corresponding carboxylic acids is effected by merging a Cu-catalyzed oxidation using O2 as a terminal oxidant with a subsequent chlorite oxidation (Lindgren oxidation). The protocol was optimized to obtain pure products without chromatography or crystallization. Interception at the aldehyde stage allowed for Z/E-isomerization, thus rendering the oxidation stereoconvergent with respect to the configuration of the starting material

Crossed intramolecular Rauhut−Currier-type reactions via dienamine activation

Trabajo presentado como póster al 3.Tag der Chemie celebrado en Dortmund (Alemania) en 2010.The intramolecular Rauhut−Currier reaction creates a carbon−carbon bond between two tethered Michael acceptors. Previous asymmetric versions have relied on 1,4-additions of chiral nucleophilic catalysts. Herein, we investigate a novel strategy that involves the formation of electron rich dienamines as key intermediates. Our methodology provides an efficient entry to the iridoid framework.Financial support was provided by the DFG (SPP1179), the Fonds der Chemischen Industrie (Dozentenstipendium to M. C.), the Alexander von Humboldt Foundation (fellowship to E. M.-L.) and the Aragón I+D Foundation and the Spanish Ministry of Science and Innovation (Programa Nacional de Movilidad de Recursos Humanos del Plan Nacional de I-D+I 2008-2011) and CSIC (PIE 200880I260) (R. P. H.).Peer Reviewe

Crossed Intramolecular Rauhut−Currier-Type Reactions via Dienamine Activation

International audienceThe intramolecular Rauhut-Currier reaction creates a carbon-carbon bond between two tethered Michael acceptors. Previous asymmetric versions have relied on 1,4-additions of chiral nucleophilic catalysts. Herein, we investigate a novel strategy that involves the formation of electron rich dienamines as key intermediates. Our methodology provides an efficient entry to the iridoid framework