β‑Aryl-α-nitro-α,β-enals as Heterodienes and Dienophiles

As demonstrated with the β-(2-furyl)-substituted analogue 1b, β-aryl-α-nitro-α,β-enals (1) behave as heterodienes against enamines and enol ethers using their enal unit (e.g., 1b → 12). α-Nitro-α,β-enals can act as well as highly reactive dienophiles to render adducts endowed with nitrogenated quate...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-09, Vol.79 (18), p.8645-8651
Main Authors: Lago-Santomé, Hugo, Martínez-Bescos, Patricia, Fernández-González, Marta, Ozores-Viturro, Lidia, Cagide-Fagín, Fernando, Alonso, Ricardo
Format: Article
Language:English
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Summary:As demonstrated with the β-(2-furyl)-substituted analogue 1b, β-aryl-α-nitro-α,β-enals (1) behave as heterodienes against enamines and enol ethers using their enal unit (e.g., 1b → 12). α-Nitro-α,β-enals can act as well as highly reactive dienophiles to render adducts endowed with nitrogenated quaternary centers (e.g., 1b → 15a). A hetero-Diels–Alder (HDA)/Diels–Alder (DA) sequence from 1b also proved feasible on serial treatment with ethyl vinyl ether and Danishefsky’s diene (1b → 14).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo501418u