ChemInform Abstract: Diastereoselective Alkylation of the Dianion of 5-Ethoxy-4(S)-hydroxy- 1-isopropyl-2-pyrrolidinone. Synthesis of Enantiomerically Pure Azabicycles.

ChemInform Abstract

(S)-Malic acid (I) is converted to the pyrrolidinone (IV). Lithiation gives the dilithio compound (V) which reacts with the electrophiles (VI), yielding the substituted compounds (VII). The alkynyl derivatives (VIIc) - (VIIe) cyclize on treatment with formic acid to produce mixtures of the allenic compounds (VIII) - (X). (Intermediates).