Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.