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Synfacts 2011(9): 1014-1014
DOI: 10.1055/s-0030-1260915
DOI: 10.1055/s-0030-1260915
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Intermolecular Stetter Reaction of Enals with Nitroalkenes
D. A. DiRocco, T. Rovis*
Colorado State University, Fort Collins, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. August 2011 (online)
Significance
An asymmetric intermolecular Stetter reaction of enals 2 with nitroalkenes 3 catalyzed by chiral N-heterocyclic carbenes has been developed. With precatalyst 1, the reaction proceeded with good to high enantioselectivity and afforded good yields of Stetter products 4. The presence of catechol as an additive was crucial for the reaction efficiency. This effect of a bifunctional Brønsted acid has also been observed in the intramolecular Stetter reaction and could be general, enabling lower catalyst loadings in other N-heterocyclic carbene catalyzed transformations. Primary alkyl-substituted nitroalkenes are not suitable substrates for the current catalytic system.