3 years ago

Asymmetric Synthesis of Chiral Acyclic Purine Nucleosides Containing a Hemiaminal Ester Moiety via Three-Component Dynamic Kinetic Resolution

Asymmetric Synthesis of Chiral Acyclic Purine Nucleosides
Containing a Hemiaminal Ester Moiety via Three-Component Dynamic Kinetic
Resolution
Xiao-Xia Wu, Hai-Ming Guo, Ming-Sheng Xie, Gui-Rong Qu, Yang-Guang Chen
An efficient route to construct chiral acyclic purine nucleosides containing a hemiaminal ester moiety is reported via three-component dynamic kinetic resolution of purines, aldehydes, and acid anhydrides. The procedure provides diverse chiral acyclic purine nucleoside analogues in a regioselective manner with good yields (up to 93% yield) and excellent enantioselectivities (up to 95% ee). Furthermore, the chiral (acyloxyalkyl)-5-fluorouracil could also be generated as a potential prodrug of 5-fluorouracil.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b00135

DOI: 10.1021/acs.orglett.8b00135

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