Starting from N-protected cis- and trans-2-aminocyclopent-3-enecarboxylic acid derivatives, isomers of 2-amino-3-hydroxycyclopentanecarboxylic acid (8 and 12) were prepared via oxazoline intermediates, whereas the stereoisomeric 2-amino-3,4-dihydroxycyclopentanecarboxylic acids 14 and 17 were synthesized by OsO4-catalyzed oxidation. The enantiomers of 8 and 14 were also prepared by the same pathway. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR spectroscopy.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry