Département de chimie moléculaire

A highly selective N-sulfinylimidate aldolization has been developed under mildly basic conditions leading to diastereopure products of high synthetic potential [e.g., E-sulfinylimidate I + PhCHO in presence of TiCl₂(OiPr)₂ and Et₃N afforded aldol II with 97:3 dr (relative to the beta-diastereomeric alc.)]. The innate reversibility of this aldolization was suppressed by the use of titanium as the Lewis acid. An application of this methodol. via the synthesis of a potential neurotransmitter reuptake inhibitor is illustrated.