Diastereoselectivity of the reactions of organometallic reagents with protected D- and L-erythrulose 1,3-O-ethylidene acetals

1,3-O-Ethylidene acetals of D- and L-erythrulose bearing various protecting groups on the 4-OH group have been prepared using D-glucose as the starting material. The stereo-selectivity of the additions of several organometallic reagents to the carbonyl group of these compounds has then been investigated. In contrast to previously studied erythrulose derivatives, the type of protecting group does not play a significant role in the stereocontrol of the process. Theoretical calculations have been performed in order to find an explanation of this behaviour. (C) 1997 Elsevier Science Ltd.