Events The 1st International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-1-02005

This submission belongs to the session a. General Organic Synthesis of the event The 1st International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Sep, 1997

Citation

T. Tejero, F. L. Merchan, S. Franco, P. Merino, Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-b-Hydroxy Aspartic Acid., in Proceedings of The 1st International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1997, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-1-02005

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

P. Merino ¹

S. Franco ¹

F. L. Merchan ¹

T. Tejero ¹

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.

(S)-6-Isopropyl-5-Phenyl-1,2,3,6-Tetrahydro-2-Pyrazinone: A New Chiral Glycine Equivalent for the Synthesis of (Z)-a,b-Didehydro-a-Amino Acid Derivatives

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