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

[ Vol. 15 , Issue. 5 ]

Author(s):

Sven Mangelinckx*, Sietske Peeters and Norbert De Kimpe   Pages 349 - 351 ( 3 )

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.

Affiliation:

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

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