Synthesis of Regio- and Stereoisomers of Highly Functionalized 1,2,3- Triazole-substituted Cyclopentanes

Title: Synthesis of Regio- and Stereoisomers of Highly Functionalized 1,2,3- Triazole-substituted Cyclopentanes

Volume: 8 Issue: 3

Author(s): Lorand Kiss, Eniko Forro and Ferenc Fulop

Affiliation:

Keywords: Amino alcohols, azides, carbocyclic nucleosides, click chemistry, 1,3-dipolar cycloaddition, enzymes, 1,2,3- triazoles, antiviral activity, Triazole-modified, multifunctionalized cyclopentanes

Abstract: Highly functionalized regio- and stereoisomers of 1,2,3-triazole-substituted cyclopentanes were prepared in six steps from either bicyclic β-lactam 7 or γ-lactam 23 by 1,3-dipolar cycloaddition of the azido cyclopentanol intermediates with acetylenes. The reactions of azido aminocyclopentanols with non-symmetric acetylenes resulted regioselectively in the corresponding 1,4-disubstitued triazole derivatives under both thermal and Cu(I)-catalysed conditions. These compounds can be regarded as highly functionalized 1,2,3-triazole-modified carbocyclic nucleoside analogues.

Cite this article as:

Kiss Lorand, Forro Eniko and Fulop Ferenc, Synthesis of Regio- and Stereoisomers of Highly Functionalized 1,2,3- Triazole-substituted Cyclopentanes, Letters in Organic Chemistry 2011; 8(3) . https://dx.doi.org/10.2174/157017811795038359