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Note | Special issue | Vol 82, No. 2, 2010, pp.1727-1737
Published online, 2nd November, 2010
DOI: 10.3987/COM-10-S(E)119
Asymmetric Intramolecular Aldol Reaction Mediated by (S)-N-Substituted-N-(2-pyrrolidinylmethyl)amine to Prepare Wieland-Miescher Ketone

Yuichi Akahane, Kohei Inomata,* and Yasuyuki Endo

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


New or known N-substituted-N-(2-pyrrolidinylmethyl)amine deriva- tives 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.