Diastereoselective Conjugate Addition of Cyanide to α,β‐Unsaturated Oxazolidinones: Enantioselective Synthesis of ent‐Pregabalin and Baclofen.

Abstract

Diastereoselective Conjugate Addition of Cyanide to α,β-Unsaturated Oxazolidinones: Enantioselective Synthesis of ent-Pregabalin and Baclofen. -A diastereoselective method is developed for the selective hydrocyanation of α,β-unsaturated carbonyl compounds bearing a chiral oxazolidine auxiliary. The products (IIIb) and (IIId) are transformed to ent-pregabalin (VI) and (S)-baclofen (VIII). -(ARMSTRONG*, A.; CONVINE, N. J.; POPKIN, M. E.; Synlett 2006, 10, 1589-1591; Dep. Chem., Imp. Coll., London SW7 2AZ, UK; Eng.) -Mais 43-044