American Chemical Society
ol7b01221_si_001.cif (1.78 MB)

Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations

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posted on 2017-05-30, 21:29 authored by Zhen Wang, Huacheng Xu, Qin Su, Ping Hu, Pan-Lin Shao, Yun He, Yixin Lu
A phosphine-catalyzed novel enantioselective [4 + 2]-annulation reaction between allene ketones and 1-azadienes has been developed, and tetrahydropyridines were obtained in good yields and with excellent enantioselectivities. Subsequent exposure of tetrahydropyridines to benzyne leads to a [2 + 2]-cyclization, creating optically enriched polycyclic piperidines with a quaternary stereogenic center and a cyclobutene moiety. The reported stepwise [4 + 2]/[2 + 2]-cycloadditions represent a new approach to access enantiomerically enriched nitrogen-containing six-membered ring systems.