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Phosphine-Catalyzed Highly Enantioselective [3 + 3] Cycloaddition of Morita–Baylis–Hillman Carbonates with C,N-Cyclic Azomethine Imines

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journal contribution
posted on 08.04.2015, 00:00 authored by Lei Zhang, Honglei Liu, Guanyu Qiao, Zhanfeng Hou, Yang Liu, Yumei Xiao, Hongchao Guo
The first phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita–Baylis–Hillman carbonates with C,N-cyclic azomethine imines is described. Using a spirocyclic chiral phosphine as the catalyst, a novel class of pharmaceutically interesting 4,6,7,11b-tetrahydro-1H-pyridazino­[6,1-a]­iso-quinoline derivatives were obtained in high yields with good to excellent diastereoselectivities and extremely excellent enantioselectivities (98–>99% ee).