"Syn-effect” in asymmetric vinylogous alkylation of 3-[4-(N-phthalimide)-but-2-enoyl]oxazolidinone

Abstract

An asymmetric vinylogous alkylation reaction of a N-enoyl oxazolidinone where an N-protected -nitrogen atom is linked to the unsaturated system is described. This reaction gave -alkylated products in moderate yields and moderate diastereomeric ratios regarding the newly formed stereogenic center. Concomitantly, a deconjugated double bond was formed with a high Z-selectivity, thus representing a strong "syn-effect". The removal of chiral oxazolidinone moiety and N-deprotection of amino group furnished a chiral -substituted -amino acid.