Highly Diastereoselective Cycloadditions via Chelation Control: Asymmetric Synthesis of β-Lactones

Article abstract of DOI:10.1016/0040-4039(95)00716-P

Chelation controlled <2+2> cycloadditions of trimethylsilylketene to chiral α- and β-benzyloxyaldehydes followed by desilylation provides a highly diastereoselective route to functionalized β-lactones.Several Lewis acids were examined and MgBr2*Et2O was found to give the highest diastereoselectivities and yields.