Application of asymmetric aminohydroxylation to heteroaromatic acrylates

Furyl and thienyl acrylates could be aminohydroxylated with high selectivit y, but pyrrolyl acrylates resist aminohydroxylation under the present react ion conditions. The corresponding aminohydroxylation products, the 3-amino- 2-hydroxy-3-(2-furyl)propionate derivative and the 3-amino-2-hydroxy-3-(2-t hienyl)propionate derivative, could be easily converted to the beta-hydroxy -alpha-amino acids. The dihydropyridone obtained from the 3-amino-2-hydroxy -3-(2-furyl)propionate derivative is a chiral building block for synthesis of polyhydroxy indolizidine alkaloids. (C) 2000 Published by Elsevier Scien ce Ltd.