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Enantioselective Copper‐Catalyzed [3+3] Cycloaddition of Azomethine Ylides with Azomethine Imines
Author(s) -
Guo Hongchao,
Liu Honglei,
Zhu FuLin,
Na Risong,
Jiang Hui,
Wu Yang,
Zhang Lei,
Li Zhen,
Yu Hao,
Wang Bo,
Xiao Yumei,
Hu XiangPing,
Wang Min
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201307317
Subject(s) - cycloaddition , enantioselective synthesis , azomethine ylide , catalysis , chemistry , copper , combinatorial chemistry , yield (engineering) , organic chemistry , computer science , 1,3 dipolar cycloaddition , materials science , metallurgy
The more dipoles, the merrier : An asymmetric [3+3] cycloaddition of azomethine ylides derived from imines 1 with azomethine imines 2 in the presence of a chiral ferrocenylphosphine–copper catalyst afforded highly functionalized heterocyclic products 3 in high yield with excellent enantio‐ and diastereoselectivity (see scheme; DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene). The 1,3‐dipolar reaction partners can be readily prepared from aldehydes.