Asymmetric Synthesis of Amines by the Knochel-Type MgCl<sub>2</sub>-Enhanced Addition of Benzyl Zinc Reagents to <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines
2011-03-04T00:00:00Z (GMT) by
The MgCl<sub>2</sub>-enhanced addition of benzyl zinc reagents to <i>N</i>-<i>tert</i>-butanesulfinyl imines proceeds readily at room temperature to afford the <i>N</i>-<i>tert</i>-butanesulfinyl-protected amine products in good yields and diastereomeric ratios. This method is functional group tolerant in both the imine substrate and benzyl zinc coupling partner. Moreover, benzyl zinc reagent addition to the <i>N</i>-<i>tert</i>-butanesulfinyl imine <b>3o</b> prepared from isopropylidene-protected glyceraldehyde proceeds in high yield and with exceptional selectivity to provide rapid entry to hydroxyethylamine-based aspartyl protease inhibitors.