Speeding up heterogeneous catalysis with an improved highly reusable catalyst for the preparation of enantioenriched secondary alcohols

Abstract

A new catalytic heterogeneous system, very efficient and highly reusable, for the preparation of enantioenriched secondary alcohols through the addition of diethylzinc to benzaldehyde has been developed. This system is based on a chiral bis(hydroxyamide) ligand supported on crosslinked polystyrene. The catalyst has been shown to be very efficient, leading to the corresponding secondary alcohol with an enantiomeric excess of 93% in a time as short as 2h and using just 4% of the heterogeneous catalyst and just 1.5 equivalents of the organozinc reagent. We have demonstrated that the new catalyst is very stable and can be efficiently recycled with no decrease in yield or enantioselectivity. The presented system has an unquestionable interest for the potential transfer of the reaction to the industry by using catalytic fluidized-bed reactors.