Catalytic Asymmetric Intermolecular Stetter Reaction of Enals with Nitroalkenes: Enhancement of Catalytic Efficiency through Bifunctional Additives
Journal of the American Chemical SocietyPublished 16 June 2011
Daniel A. DiRocco, Tomislav Rovis
Citations225
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
The impact of catechol has been found to be general, facilitating far lower catalyst loadings than were previously achievable and affords good yields of the Stetter product.
Abstract
An asymmetric intermolecular Stetter reaction of enals with nitroalkenes catalyzed by chiral N-heterocyclic carbenes has been developed. The reaction rate and efficiency are profoundly impacted by the presence of catechol. The reaction proceeds with high selectivities and affords good yields of the Stetter product. Internal redox products were not observed despite of the protic conditions. The impact of catechol has been found to be general, facilitating far lower catalyst loadings than were previously achievable.
Keywords
Chemistry
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