Favoring trienamine activation through unconjugated dienals: organocatalytic enantioselective remote functionalization of alkenes.
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.
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea UPV/EHU, P.O. Box 644, 48080 Bilbao (Spain).
Liher
L
Prieto
Garazi
G
Talavera
Uxue
U
Uria
Efraim
E
Reyes
Jose L
JL
Vicario
Luisa
L
Carrillo
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D000588:Amines
asymmetric catalysis; cycloaddition; organocatalysis; trienamines; vinylogy