Abstract
Cyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory.
1 Introduction
2 Biological Relevance of the cis-1,3-Diamine Motif
3 Classical Synthetic Strategies towards cis-1,3-Diamines
4 N–N Bond Cleavage of Bicyclic Hydrazines: A Versatile Method to Access cis-1,3-Diamines
4.1 Preparation of Five-Membered Cyclic cis-1,3-Diamino Alcohols
4.2 Access to Fluorinated 1,3-cis-Diaminocyclopentanes
4.3 Synthesis of cis-1,3-Diaminocyclohexitols
4.4 Formation of Cyclic cis-3,5-Diaminopiperidines
5 Applications of Cyclic cis-1,3-Diamines
5.1 Small-Molecular RNA Binders
5.2 Fluorinated 1,3-Diamino Cyclopentanes as NMR Probes
6 Concluding Remarks
Key words
cyclic
cis-1,3-diamines - bicyclic hydrazines - fragments RNA ligands and probes - N–N bond cleavage - hydroxylation - fluorination - reductive amination
