Palladium-catalyzed asymmetric allylic alkylation (AAA) has turned out to be an extremely useful and versatile method for carbon-carbon bond formation.[1] Here we present the palladium-catalyzed kinetic resolution of 1,3-disubstituted unsymmetrical allylic acetates, using silyl enol ether TMSOF as nucleophile to access 3-substituted-?-butenolide for the first time (Figure 1). Preliminary studies showed that the hydrogen bonding interactions play a key role in controling the enantio- and regio- selectivity. An unusual reactivity profile of TMSOF was also observed during this investigation.

Highly enantioselective synthesis of 3-substituted-<i>γ</i>-butenolide via palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates

243rd National Meeting (2012)

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Highly enantioselective synthesis of 3-substituted-γ-butenolide via palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates