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Enantioselective Copper‐Catalyzed [3+3] Cycloaddition of Azomethine Ylides with Azomethine Imines

2013; Wiley; Volume: 52; Issue: 48 Linguagem: Inglês

10.1002/anie.201307317

1521-3773

Hongchao Guo, Honglei Liu, Fu‐Lin Zhu, Risong Na, Hui Jiang, Yang Wu, Lei Zhang, Zhen Li, Hao Yu, Bo Wang, Yumei Xiao, Xiang‐Ping Hu, Min Wang,

Asymmetric Synthesis and Catalysis

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. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.