Enantioselective synthesis of β-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: Application to the synthesis of (R)-(-)-baclofen

Article abstract of DOI:10.1016/S0957-4166(97)00538-7

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 γ,δ-unsaturated ester (S,E)-(+)-6 with high stereoselectivity. This latter derivative is converted into (R)-(-)-baclofen through a high yield one-pot reaction.