Asymmetric Intramolecular Aldol Reaction Mediated by (S)-N-Substituted-N-(2-pyrrolidinylmethyl)amine to Prepare Wieland-Miescher Ketone

Abstract

New or known N-substituted-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of alkyl and aryl substituents were easily prepared from N-Boc-proline or N'-Boc-N-(2-pyrrolidinylmethyl)amine.The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and TFA to prepare Wieland-Miescher ketone was examined.During the examination, optimal amount of TFA in the reaction was identified.