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Application of asymmetric aminohydroxylation to heteroaromatic acrylates

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
11
Issue
16
Identifiers
DOI: 10.1016/s0957-4166(00)00308-6

Abstract

Abstract Furyl and thienyl acrylates could be aminohydroxylated with high selectivity, but pyrrolyl acrylates resist aminohydroxylation under the present reaction conditions. The corresponding aminohydroxylation products, the 3-amino-2-hydroxy-3-(2-furyl)propionate derivative and the 3-amino-2-hydroxy-3-(2-thienyl)propionate derivative, could be easily converted to the β-hydroxy-α-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.

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