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Issue 48, 2018
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Organocatalytic enantioselective synthesis of acyclic pyrimidine nucleosides by aza-Michael reaction

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Abstract

An efficient diarylprolinol triphenylsilyl ether-catalyzed enantioselective aza-Michael reaction of pyrimidines as N-centered nucleophiles to α,β-unsaturated aldehydes, followed by reduction, provided chiral acyclic pyrimidine nucleosides in good yields (51–78% yields for two steps) and excellent enantioselectivities (91–98% ee). In addition, the chiral acyclic pyrimidine nucleoside having the tert-butyldiphenylsilyl-protected hydroxyl substituent was successfully applied to the synthesis of the corresponding chiral cyclic pyrimidine nucleoside analogue bearing the tetrahydrofuranyl ring.

Graphical abstract: Organocatalytic enantioselective synthesis of acyclic pyrimidine nucleosides by aza-Michael reaction

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Article information


Submitted
06 Nov 2018
Accepted
27 Nov 2018
First published
27 Nov 2018

Org. Biomol. Chem., 2018,16, 9477-9486
Article type
Paper

Organocatalytic enantioselective synthesis of acyclic pyrimidine nucleosides by aza-Michael reaction

S. Lee, J. Ahn, J. Seo, H. Ha and C. Cho, Org. Biomol. Chem., 2018, 16, 9477
DOI: 10.1039/C8OB02754D

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