Electrogenerated chiral 4-methoxy-2-oxazolidinones as diastereoselective amidoalkylation reagents for the synthesis of beta-amino alcohol precursors

A flexible and efficient synthesis of enantiomerically pure 4,5-substituted 2-oxazolidinones - important target molecules as precursors of pharmacolog ically active 2-oxazolidinones, p-amino alcohols, P-blockers and azasugar d erivatives - is described. As starting materials, the enantiopure storage f orms of chiral N-acyliminium ions (4RS,5S)-5-chloromethyl-4-methoxy-1,3-oxa zolidin-2-one (2) and (4RS,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one (3) were used; these are readily available from the chiral pool with the aid of electrochemical transformations. Substitution of the 4-methoxy group in bu ilding blocks 2 and 3 with a large variety of organometallic nucleophiles r esulted in the trans-diastereoselective formation of enantiopure 4,5-disubs tituted 2-oxazolidinones, with a high degree of flexibility in the substitu ent at the 4-position.