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Electrophilic amination: Enantioselective syntheses of d-allothreonine and l-threonine

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
29
Issue
51
Identifiers
DOI: 10.1016/s0040-4039(00)82449-1

Abstract

Abstract Starting from inexpensive polyhydroxybutanoate (PHB), D-allothreonine 1 and L-threonine 2 were synthetized by a sequence involving a diastereoselective electrophilic amination. When (R) 3-hydroxybutanoic acid was protected as dioxanone 9 very good yield (>95 %) and high diastereomeric excess (>99 %) were obtained in the amination step.

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