3 years ago

Organocatalytic Synthesis of 4-Aryl-1,2,3,4-tetrahydropyridines from Morita-Baylis-Hillman Carbonates through a One-Pot Three-Component Cyclization

Organocatalytic Synthesis
of 4-Aryl-1,2,3,4-tetrahydropyridines
from Morita-Baylis-Hillman Carbonates through a One-Pot Three-Component
Cyclization
Hongbin Zhai, Bin Cheng, Yun Li, Huifei Wang, Cheng Tao, Jian Wei, Yuntong Li
An efficient DABCO-catalyzed three-component formal [3 + 2 + 1] annulation, involving a Morita-Baylis-Hillman carbonate, a 1,3-ketoester, and a primary amine, leading to one-pot synthesis of substituted 4-aryl-1,2,3,4-tetrahydropyridines, has been developed. The densely functionalized products were generally obtained in good to excellent yields under mild conditions. The structures including the relative stereoconfigurations of the representative products were confirmed by X-ray diffraction analysis.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02818

DOI: 10.1021/acs.joc.7b02818

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