Claus‐Juergen Koch, G. Höfner, K. Polborn
Jun 1, 2003
Citations
0
Influential Citations
15
Citations
Journal
European Journal of Organic Chemistry
Abstract
A synthesis of all four stereoisomers [(1S,2S)-, (1R,2R)-, (1S,2R)-, (1R,2S)-] of 1-amino-2-(hydroxymethyl)cyclobutanecarboxyclic acid is presented. The synthesis is based on the chiral glycine equivalent 1, employed in both enantiomeric forms. The key step involves the cyclization of the silyl-protected iodohydrins 5a−d to the corresponding spiro derivatives 6a−d with the aid of the phosphazenic base tBu-P4. The final compounds were found to display moderate potency as ligands for the glycine binding site of the NMDA receptor. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)