Convenient asymmetric synthesis of 3(S)-3-[(R)-1′-tert-butyldimethylsilyloxyethyl]-5-hydroxypyrrolidon-2-one, a useful synthon for the thienamycin-like γ-lactam

Abstract

Chiral 3-substituted 5-hydroxypyrrolidin-2-one 12, useful for the synthesis of thienamycin-like γ-lactam, was successfully synthesised by utilising highly diastereoselective alkylation with the tin(II) enolate of 7 onto acetaldehyde, ammonolysis of the resultant amide 9, and oxidative cyclisation of 11.