Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine

A straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic alpha-amino-beta-keto esters by using a ATH/DKR protocol has been developed. This method gives moderate to excellent yields with high chemo-, diastereo- and enantioselectivities for a broad range of substrates. In order to highlight the versatility of the methodology it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.