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Asymmetric ruthenium-catalyzed 1,4-additions of aryl thiols to enones

Published in Organic and Biomolecular Chemistry. 2010, vol. 8, no. 1, p. 193-200
Abstract Well defined, stable, one-point binding ruthenium complexes 1 and 2 selectively bind and activate α,β-unsaturated carbonyl compounds for cycloaddition reactions. These mild Lewis acids catalyze asymmetric 1,4-addition reactions of aryl thiols to enones with product selectivities up to 87% ee. 31P NMR experiments provide an insight into the intricate equilibria governing the reaction mechanism. The absolute configuration of the major products indicates enones to react in the syn-s-trans orientation. Models based on X-ray structures of the Ru complexes can be used to rationalize selectivity.
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BADOIU, Andréi et al. Asymmetric ruthenium-catalyzed 1,4-additions of aryl thiols to enones. In: Organic and Biomolecular Chemistry, 2010, vol. 8, n° 1, p. 193-200. doi: 10.1039/b918877k https://archive-ouverte.unige.ch/unige:4864

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Deposited on : 2010-01-25

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