A concise Diastereospecific Synthesis of 3-Amino-2-hydroxy Acids

Jefford, Charles; Wang, Jian Bo; Lu, Zhi-Hui

doi:10.1016/S0040-4039(00)60398-2

Scientific article

Letter

English

A concise Diastereospecific Synthesis of 3-Amino-2-hydroxy Acids

ContributorsJefford, Charles; Wang, Jian Bo; Lu, Zhi-Hui

Published inTetrahedron Letters, vol. 34, no. 47, p. 7557-7560

Publication date1993

Abstract

L-Aspartic acid by N-tosylation, anhydride formation, reduction, α-hydroxylation, iodo esterification and alkylation followed by saponification and deprotection afforded a series of 4-alkyl-3-amino-2-hydroxybutyric acids having the 2S,3R configuration (de>95%).

Keywords

Aspartic acid
Diastereoselective hydroxylation

Affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Funding

Swiss National Science Foundation - 20-32'166.91

Citation (ISO format)

JEFFORD, Charles, WANG, Jian Bo, LU, Zhi-Hui. A concise Diastereospecific Synthesis of 3-Amino-2-hydroxy Acids. In: Tetrahedron Letters, 1993, vol. 34, n° 47, p. 7557–7560. doi: 10.1016/S0040-4039(00)60398-2

Article (Published version)

Identifiers

PID : unige:152038
DOI : 10.1016/S0040-4039(00)60398-2

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900603982

ISSN of the journal0040-4039

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A concise Diastereospecific Synthesis of 3-Amino-2-hydroxy Acids

L-Aspartic acid by N-tosylation, anhydride formation, reduction, α-hydroxylation, iodo esterification and alkylation followed by saponification and deprotection afforded a series of 4-alkyl-3-amino-2-hydroxybutyric acids having the 2S,3R configuration (de>95%).

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