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Regio‐ and Enantioselective [3+2] Cycloaddition of α‐Purine Substituted Acrylates with Allenes: An Approach to Chiral Carbocyclic Nucleosides
Author(s) -
Gao YaoWei,
Niu HongYing,
Zhang QiYing,
Xie MingSheng,
Qu GuiRong,
Guo HaiMing
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800523
Subject(s) - chemistry , stereocenter , enantioselective synthesis , annulation , acrylate , stereochemistry , cycloaddition , phosphine , yield (engineering) , nucleoside , benzimidazole , purine , organic chemistry , catalysis , polymer , materials science , monomer , metallurgy , enzyme
N ‐Heteroaromatic substituted acrylates are employed in the phosphine‐catalyzed [3+2] annulation with allenes for the first time, affording regiospecific carbocyclic nucleoside analogues in an α‐addition manner. Various chiral carbocyclic nucleoside analogues containing a quaternary stereocenter and a C=C double bond are generated in good yields (up to 90% yield) and excellent enantioselectivities (up to 97% ee). α‐Purine‐containing disubstituted acrylate and α‐benzimidazole substituted acrylate are also suitable substrates for this reaction.