Enantioselective Synthesis of α-Alkyl-α,β-dihydroxy Esters

Significance

The enantioselective synthesis of α-alkyl-α,β-dihydroxy carboxylic acids and esters has traditionally relied on dihydroxylation of the corresponding unsaturated ester. However, these methods are typically lengthy and the presence of other alkene functionalities presents additional challenges. The authors report an asymmetric tandem 1,2-Wittig rearrangement-aldol reaction effected through use of chiral auxiliary 2-phenylcyclohexanol. Reaction of various esters with aldehydes provides these highly functionalized dihydroxy esters in excellent yields and selectivities.