Conjugate addition of cyanide to chiral a,b-unsaturated oxazolidinones catalyzed by samarium(III) isopropoxide proceeds with good diastereoselectivity. The addition products can be converted into the biologically active targets ent-pregabalin and baclofen.

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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

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