A Concise Stereoselective Synthesis of 2-Substituted 1-Aminocyclopropanecarboxylic Acids

Printer-friendly version
TitleA Concise Stereoselective Synthesis of 2-Substituted 1-Aminocyclopropanecarboxylic Acids
Publication TypeJournal Article
Year of Publication2009
AuthorsPradhan, TK, Joosten A, Vasse JL, Bertus P, Karoyan P, Szymoniak J
JournalEuropean Journal of Organic Chemistry
Issue29
Pagination5072-5078
Date PublishedOct
ISBN Number1434-193X
Accession NumberISI:000271010600020
Abstract

A simple and stereoselective method for the preparation of (Z)-2-substituted 1-aminocyclopropanecarboxylic acids is described. The common key step for these reaction sequences involves the stereoselective Ti-mediated coupling of benzyloxy nitrile and homoallylic alcohol. The resulting 2-hydroxyethyl-substituted cyclopropylamine can be transformed shortly into various cyclopropane amino acid analogues on the gram scale, in good overall yields. Several syntheses of 2,3-methanoamino acids, that is, ACCs derived from proteinogenic alpha-amino acids or analogues, such as glutamic acid, arginine, homoarginine, and lysine derivatives are presented to exemplify the usefulness of the method. Additionally, starting from cyanoesters, spirocyclopropane gamma-amino acid analogues are available in this way. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

URL<Go to ISI>://000271010600020
DOI10.1002/ejoc.200900656
Short TitleA Concise Stereoselective Synthesis of 2-Substituted 1-Aminocyclopropanecarboxylic Acids
Unit: 
Departement