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

Andrei Bădoiu; Gerald Bernardinelli; Céline Besnard; E. Peter Kündig

doi:10.1039/B918877K

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Organic & Biomolecular Chemistry

Issue 1, 2010

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

Andrei Bădoiu , Gerald Bernardinelli , Céline Besnard and E. Peter Kündig

Org. Biomol. Chem., 2010, 8, 193-200

DOI: 10.1039/B918877K
Received 11 Sep 2009, Accepted 07 Oct 2009
First published on the web 06 Nov 2009

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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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Organic & Biomolecular Chemistry

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

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