Enantioselective copper-catalyzed azide-alkyne click cycloaddition to desymmetrization of maleimide-based bis(alkynes).
A copper catalyst system derived from TaoPhos and CuF2 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.
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou (P. R. China).
Tao
T
Song
Li
L
Li
Wei
W
Zhou
Zhan-Jiang
ZJ
Zheng
Yuan
Y
Deng
Zheng
Z
Xu
Li-Wen
LW
Xu
alkynes; asymmetric catalysis; azides; click chemistry; copper