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Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-b-Hydroxy Aspartic Acid.
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1  Departamento de Quimica Organica, Facultad de Ciencias, ICMA, Universidad de Zaragoza, E-50009 Zaragoza, Aragon, Spain

Abstract: The nucleophilic addition of 2-furyllithium to esters derived from L-serine is described. The obtained furyl ketone 5 is stereoselectively reduced (ds>=95%) with sodium borohydride to afford the corresponding syn aminoalcohol 12 in enantiomerically pure form. Compound 12 was further converted into valuable a-hydroxy-[beta]-amino acids by means of the furan-to-acid equivalence.
Keywords: L-Serine, Furan, Furylketones, Hydroxyaminoacids, Aspartic Acid.