Rh-Catalyzed Asymmetric Hydrogenation of β-Substituted-β-thio-α,β-unsaturated Esters: Expeditious Access to Chiral Organic Sulfides

Organic Letters
Gang LiuXumu Zhang

Abstract

Rh/bifunctional bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydorgenation of both ( Z)- and ( E)-isomers of β-substituted-β-thio-α,β-unsaturated esters was successfully developed. This new asymmetric catalytic methodology provided highly efficient access to two enantiomers of chiral organic sulfides ethyl β-substituted-β-thio-propanoates with excellent results (up to 99% yield and >99% ee for ( Z)-substrates, up to 99% yield and 98% ee for ( E)-substrates, TON up to 5000), which are important intermediates in organic synthesis.

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Citations

Oct 10, 2018·Chemistry, an Asian Journal·Nilesh R Mote, Samir H Chikkali
Jan 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Franz SteppelerJacek Wojaczyński
Mar 24, 2020·Chemical Society Reviews·Luca MassaroPher G Andersson

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