Diastereoselective radical mediated alkylation of a chiral glycolic acid derivative

Radical alkylation of 2-(tert-butyl)-2-methyldioxolan-4-one, a chiral equivalent of glycolic acid, occurs with good to high diastereoselectivity that compares favorably with the corresponding enolate alkylation. The importance of the position of the transition state position, early or late, is highlighted.