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Enantioselective synthesis of β-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: application to the synthesis of (R)-(-)-baclofen
A three step synthesis of (R)-(-)-baclofen is described. The key step is the orthoester Claisen rearrangement of enantiopure allylic alcohol (S,E)-(-)-1a, affording y,δ-unsaturated ester (S,E)-(+)-6 with high stereoselectivity. This latter derivative is converted into (R)-(-)-baclofen through a high yield one-pot reaction.