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Paper

Org. Biomol. Chem., 2010, 8, 193 - 200, DOI: 10.1039/b918877k

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

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

Well defined, stable, one-point binding ruthenium complexes 1 and 2 selectively bind and activate ,-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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