Oxindoles are attractive synthetic targets due to the abundance of biologically active compounds containing the oxindole motif. Of particular interest are oxindoles bearing substitution at the α-position.<br/><br/>The Tsuji-Trost allylation is a well-established method for the allylation of nucleophiles, including enolates. Our group recently published the enantioselective synthesis of α-allyl-α-aryl oxindoles using a variant of this reaction. In the work presented here we outline the synthesis of enantiopure α-allylic alcohol-α-aryl oxindoles from the corresponding enolisable α-aryl oxindoles. In this palladium-catalysed intermolecular asymmetric allylic alkylation the allyl group is supplied by vinyl epoxide. The products of this reaction are particularly sterically hindered and are obtained in good yield with high enantiomeric excess. The benefit of this allyl source is the introduction of an allylic alcohol moiety at the α-position. Allylic alcohols display different reactivity to simple allyl groups and offer interesting opportunities for further functionalisation.<br/><br/>The α-aryl oxindole substrates are accessed from isatin through an efficient metal-free one-pot two-step arylation strategy devised in our lab.

Catalytic enantioselective synthesis of α-allylic alcohol-α-aryl oxindoles

2019 Fall National Meeting

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