Attainment of syn-selectivity for boron-mediated asymmetric aldol reactions of carboxylic esters

Article abstract of DOI:10.1016/S0040-4039(98)00123-3

A new chiral reagent for syn-selective aldol reactions has been developed based on the recent finding that the stereochemistry of the boron-mediated aldol reaction of a carboxylic ester is controlled by the bulkiness of the alcohol moiety of the ester, by the proper choice of reagents, and by the enolization conditions. This readily available, inexpensive reagent has been utilized in studies directed towards the synthesis of the macrolide tedanolide.