Enantioselective synthesis of α-amino acetals (aldehydes) via nucleophilic 1,2-addition to chiral 1,3-oxazolidines

Article abstract of DOI:10.1016/S0040-4039(00)78325-0

A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91-100% de). The resulting amino alcohols 6 may be oxidatively or reductively cleaved to enantiomerically enriched α-amino acetals 3 which are useful chiral building blocks.