Asymmetric construction of nitrogen-containing [2.2.2] bicyclic scaffolds using N-( p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide.
An organocatalyzed approach to enantioenriched isoquinuclidines and bicyclo[2.2.2]octanes via a p-dodecylphenylsulfonamide-modified proline catalyst has been developed. A series of aromatic imines have been explored for the formation of isoquinuclidines with high levels of enantioselectivity and diastereoselectivity, strongly favoring the exo product. A series of aliphatic imines has also been explored, which provide access to bicyclo[2.2.2]octanes through a novel mechanistic pathway in high levels of enantioselectivity and diastereoselectivity, favoring the endo product.
Yang
Hua
H
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
Carter
Rich G
RG