Title

Proline Sulfonamide-Catalyzed, ­Domino Process for Asymmetric Synthesis of Amino- and Hydroxy-Substituted Bicyclo[2.2.2]octanes

Document Type

Article

Abstract

A generalized method for accessing highly functionalized amino-substituted bicyclo[2.2.2]octanes via p-dodecylphenylsulfonamide catalyst in a good enantio- and diastereoselective fashion has been developed. A discussion of the mechanistic underpinnings of this transformation is presented. Finally, an unexpected discovery enabling the extension of this protocol to the synthesis of OH-substituted bicyclo[2.2.2]octanes with encouraging levels of stereoselectivity is discussed.