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Scandium‐Triflate‐Catalyzed Regioselective Ring Opening of Purines with Aminocyclopropanes
Author(s) -
Liang Tao,
Xie MingSheng,
Qu GuiRong,
Guo HaiMing
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900227
Subject(s) - chemistry , regioselectivity , ring (chemistry) , catalysis , nucleoside , stereochemistry , purine metabolism , cyclopropane , trifluoromethanesulfonate , scandium , combinatorial chemistry , medicinal chemistry , organic chemistry , enzyme
An efficient route to acyclic purine nucleoside analogues with an amino group at the C1′ position of the side chains has been reported. Using Sc(OTf) 3 as the catalyst, the ring‐opening reaction of purines with aminocyclopropanes afforded acyclic nucleoside analogues with moderate to good yields and in a regioselective manner. Furthermore, phenyl cyclopropane also gave the desired acyclic nucleoside analogue with a phenyl linked at C1′ position. Furthermore, generation of a penciclovir analogue may also occur from the ring‐opening product via a reduction reaction.