Tandem hydroboration/reduction of trisubstituted β,γ-unsaturated esters for the asymmetric synthesis of chiral 1,3-diols

Treatment of a range of trisubstituted β,γ-unsaturated esters with 2 equiv of (−)-monoisopinocampheylborane results in hydroboration of their alkene functionalities and reduction of their ester groups to afford chiral 1,3-diols containing two new vicinal β,γ-(anti)-stereocentres in 67–85% enantiomeric excess.