Favoring trienamine activation through unconjugated dienals: organocatalytic enantioselective remote functionalization of alkenes.

Abstract

Unconjugated 2,5-dienals are more reactive substrates than the corresponding fully conjugated α,β,γ,δ-unsaturated aldehydes towards organocatalytic activation through trienamine intermediates. This difference in reactivity has been demonstrated in the Diels-Alder reaction with nitroalkenes, a reaction that proceeds with clean β,ε-selectivity to afford the final products in high yields and stereoselectivities, the related polyconjugated 2,4-dienals being completely unreactive.

DOI: 10.1002/chem.201304666

Cite this paper

@article{Prieto2014FavoringTA, title={Favoring trienamine activation through unconjugated dienals: organocatalytic enantioselective remote functionalization of alkenes.}, author={Liher Prieto and Garazi Talavera and Uxue Uria and Efra{\'i}m Reyes and Jose L Vicario and Luisa Carrillo}, journal={Chemistry}, year={2014}, volume={20 8}, pages={2145-8} }