Stereoselective Synthesis of 1-Amino-2-azidocyclopropanecarboxylic Acid Derivatives

Title:Stereoselective Synthesis of 1-Amino-2-azidocyclopropanecarboxylic Acid Derivatives

Volume: 15 Issue: 5

Author(s): Sven Mangelinckx*, Sietske Peeters and Norbert De Kimpe

Affiliation:

• Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, B-9000 Ghent,Belgium

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

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.

Cite this article as:

Mangelinckx Sven *, Peeters Sietske and De Kimpe Norbert , Stereoselective Synthesis of 1-Amino-2-azidocyclopropanecarboxylic Acid Derivatives, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178614666171130162824