Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates.A formal asymmetric synthesis of (+)-sertraline

The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N (dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOS P)(4)) can be effectively carried out on cyclohexadienes, leading to the as ymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates wi th cyclohexadienes results in an unprecedented carbenoid reaction that is f ormally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a forma l asymmetric synthesis of (+)-sertraline.