Synthesis of 2-pyridyl oxazoline esters and their organocatalytic application to the enantioselective silane reduction of ketones

The synthesis of a number of novel chiral 2-pyridyl oxazoline esters is reported along with the use of these in the enantioselective organocatalytic reduction of ketones. The chiral alcohols were prepared in good to excellent yields (up to 99%) and were found to catalyse the reduction reactions with good conversions (up to 99%) and in moderate to good enantioselectivies (up to 65% at high conversion and 70% with lower reactivity). The results give an insight into the effects of the catalyst structure on the selectivity observed in the reaction.