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Enantioselective Copper‐Catalyzed Azide–Alkyne Click Cycloaddition to Desymmetrization of Maleimide‐Based Bis(alkynes)
Author(s) -
Song Tao,
Li Li,
Zhou Wei,
Zheng ZhanJiang,
Deng Yuan,
Xu Zheng,
Xu LiWen
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405420
Subject(s) - cycloaddition , desymmetrization , stereocenter , enantioselective synthesis , maleimide , chemistry , azide , succinimide , alkyne , catalysis , click chemistry , norbornene , organic chemistry , combinatorial chemistry , polymerization , polymer
A copper catalyst system derived from TaoPhos and CuF 2 was used successfully for catalytic asymmetric Huisgen [3+2] cycloaddition of azides and alkynes to give optically pure products containing succinimide‐ and triazole‐substituted quaternary carbon stereogenic centers. The desired products were obtained in good yields (60–80 %) and 85:15 to >99:1 enantiomeric ratio (e.r.) in this click cycloaddition reaction.
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