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

P. Merino; S. Franco; F. Merchan; T. Tejero

doi:10.3390/ecsoc-1-02005

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Intramolecular Aza-Wittig Reaction of Iminophosphoranes with the b-Lactam Carbonyl Group

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

P. Merino

^*,

S. Franco

F. L. Merchan

T. Tejero

¹ Departamento de Quimica Organica, Facultad de Ciencias, ICMA, Universidad de Zaragoza, E-50009 Zaragoza, Aragon, Spain

Published: 01 September 1997 by MDPI in The 1st International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-1-02005

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.

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P. Merino

S. Franco

F. Merchan

T. Tejero