Desymmetrizing hydroformylation of dialkenylcarbinols with the aid of a planar-chiral, catalyst-directing group

The desymmetrizing hydroformylation of dialkenylcarbinols has been achieved with the aid of a planar-chiral, substrate-bound catalyst-directing group - the ortho-(diphenylphosphdnyl)ferrocencylcarbonyl group (o-DPPF), This method allows the simultaneous construction of two new, vicinal stereogenic centers with high levels of stereocontrol. Optimization of the hydroformylation conditions, determination of the relative and absolute configuration of the product aldehydes (chemical derivatization and X-ray crystallographic studies), as Well as conditions for removal and recovery of the catalyst-directing o-DPPF (group are described, Furthermore, a model is presented that ratioalized the experimentally observed stereochemical result, And a new esterification protocol, which allows the formation of the sterically very hindered dialkenylcarbinol o-DPPF esters, is described.