Abstract

2-Azidocyclopropane-1,1-dicarboxylic esters were transformed into orthogonally Nprotected alkyl 1-amino-2-azidocyclopropanecarboxylates via stereoselective monosaponification and subsequent Curtius reaction. Following deprotection of the ester function or the Boc-protected amino group, the first derivatives of a novel class of conformationally constrained cyclopropane α,β-diamino carboxylic acids were made accessible.

Keywords: Cyclopropanes, α, β-diamino carboxylic acids, azides, Curtius reaction, stereoselective synthesis, 1-aminocyclopropanecarboxylic acid.

Graphical Abstract