Issue 94, 2014

A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates

Abstract

A rapid and divergent access to chiral azacyclic nucleoside analogues has been established via highly exo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylides with β-nucleobase substituted acrylates. Using 1 mol% of a chiral copper complex, various chiral azacyclic nucleoside analogues were obtained in high yields, excellent exo-selectivities and enantioselectivities (98 to >99% ee).

Graphical abstract: A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates

Supplementary files

Article information

Article type
Communication
Submitted
27 Aug 2014
Accepted
28 Sep 2014
First published
06 Oct 2014

Chem. Commun., 2014,50, 14809-14812

Author version available

A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates

Q. Yang, M. Xie, C. Xia, H. Sun, D. Zhang, K. Huang, Z. Guo, G. Qu and H. Guo, Chem. Commun., 2014, 50, 14809 DOI: 10.1039/C4CC06632D

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