β,γ-Regioselective Inverse-Electron-Demand Aza-Diels–Alder Reactions with α,β-Unsaturated Aldehydes via Dienamine Catalysis
- 21 July 2014
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 16 (15), 3986-3989
- https://doi.org/10.1021/ol501814p
Abstract
A stereoselective inverse-electron-demand aza-Diels–Alder cycloaddition process of cyclic 1-aza-1,3-butadienes and α,β-unsaturated aldehydes has been developed via dienamine catalysis. This reaction exhibits excellent β,γ-regioselectivity for enal substrates with substantial structural diversity and broad functionalities, readily producing highly enantioenriched fused piperidine derivatives and enabling efficient sequential construction of complex polycyclic frameworks.Funding Information
- Ministry of Education of the People's Republic of China (IRT13031)
- Ministry of Science and Technology of the People's Republic of China (2010CB833300)
- National Natural Science Foundation of China (21122056, 21321061, 21372160)
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