Catalytic Asymmetric Synthesis of Diarylacetates and 4,4-Diarylbutanoates. A Formal Asymmetric Synthesis of (+)-Sertraline

Abstract

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