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Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-β-Hydroxy Aspartic Acid

Departamento de Quimica Organica, Facultad de Ciencias, ICMA, Universidad de Zaragoza, E-50009 Zaragoza, Aragon, Spain
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Molecules 1998, 3(1), 26-30; https://doi.org/10.3390/30100026
Received: 1 October 1997 / Accepted: 15 January 1998 / Published: 25 January 1998
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 α-hydroxy-β-amino acids by means of the furan-to-acid equivalence. View Full-Text
Keywords: L-Serine; Furan; Furylketones; Hydroxyaminoacids; Aspartic Acid L-Serine; Furan; Furylketones; Hydroxyaminoacids; Aspartic Acid
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Merino, P.; Franco, S.; Merchan, F.L.; Tejero, T. Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-β-Hydroxy Aspartic Acid. Molecules 1998, 3, 26-30.

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