Facile regio- and diastereoselective syntheses of hydroxylated 2-aminocyclohexanecarboxylic acids

Ferenc Fülöp, Márta Palkó, Eniko Forró, Máté Dervarics, Tamás A. Martinek, Reijo Sillanpää

Research output: Article

34 Citations (Scopus)

Abstract

By means of total regio- and diastereoselective functionalizations of cis- and trans-2-amino-4-cyclohexenecarboxyric acid derivatives 1, 9, 12 and 16, isomers of 2-amino-4-hydroxycyclohexanecarboxylic acid 8 and 11, and 2-amino-5-hydroxycyclohexanecarboxylic acid 15 and 19 were prepared in good yields, via 1,3-oxazine or γ-lactone intermediates. The enantiomers of 8 and 15 were also prepared by the same pathway, resulting in products with ee > 99 %. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR, using some key vicinal couplings and characteristic NOEs.

Original languageEnglish
Pages (from-to)3214-3220
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number15
DOIs
Publication statusPublished - júl. 25 2005

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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