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

Authors: Huw M. L. Davies, Douglas G. Stafford , and Tore Hansen

Org. Lett.,

1999, 1 (2), 233–236


The intermolecular C−H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N-(dodecylbenzenesulfonyl)prolinate) (Rh2(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.

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