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Regio- and Enantioselective Synthesis of Chiral Pyrimidine Acyclic Nucleosides via Rhodium-Catalyzed Asymmetric Allylation of Pyrimidines

Author:
Liang, Lei, Xie, Ming-Sheng, Qin, Tao, Zhu, Man, Qu, Gui-Rong, Guo, Hai-Ming
Source:
Organic letters 2017 v.19 no.19 pp. 5212-5215
ISSN:
1523-7052
Subject:
allylation, carbonates, catalysts, chemical oxygen demand, chemical structure, dihydroxylation, enantioselective synthesis, enantioselectivity, nucleosides, pyrimidines
Abstract:
A direct route to branched N-allylpyrimidine analogues is herein reported via the highly regio- and enantioselective asymmetric allylation of pyrimidines with racemic allylic carbonates. With [Rh(COD)Cl]₂/chiral diphosphine as the catalyst, a range of chiral pyrimidine acyclic nucleosides could be obtained under neutral conditions in good yields (up to 95% yield) with high levels of regio- and enantioselectivities (15:1 to >40:1 B/L and up to 99% ee). Furthermore, chiral pyrimidine acyclic nucleoside bearing two adjacent chiral centers has been successfully synthesized by asymmetric dihydroxylation.
Agid:
5826968