Highly enantioselective synthesis of 3-substituted γ-butenolides by palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates

Mao, B.; Ji, Y.; Fañanás-Mastral, Mín.; Caroli, G.; Meetsma, A.; Feringa, B.L.

Angewandte Chemie 51(13): 3168-3173

ISSN/ISBN: 1521-3773

2012

PMID: 22345064

DOI: 10.1002/anie.201109075

Document: 001906169

Resolving the issue: A near-perfect Pd-catalyzed kinetic resolution of 1,3-disubstituted unsymmetrical allylic acetates uses silyl enol ethers as nucleophiles to access the important 3-substituted-furanone scaffold (see scheme; DACH=diaminocyclohexyl, dba=dibenzylideneacetone). The reaction proceeds under mild conditions and provides the desired products with excellent chemo-, regio-, and enantioselectivity.

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