Synthesis of racemic cis-1-alkyl- and 1-aryl-2-aminocyclopropanecarboxylic esters

The title cyclic beta-amino esters were synthesized stereo- and regioselectively. Starting from the corresponding 1-aryl- and 1-alkylcyclopropane-1,2-dicarboxylates, selective monosaponification and subsequent Curtius reaction leads to certain cis-1-alkyl-and 1-aryl-2-aminocyclopropanecarboxylic esters. These P-aminocyclopropanecarboxylate derivatives (beta-ACCs) can be seen as useful building blocks for beta-peptides. (C) 2003 Elsevier Science Ltd. All rights reserved.