Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric SN2′ Reaction

Journal Reference

Angewandte Chemie International Edition, Volume 54, Issue 28, pages 8263–8266, 2015.

Yusuke Kuroda,Dr. Shingo Harada,Akinori Oonishi,Dr. Yousuke Yamaoka,Prof. Dr. Ken-ichi Yamada,Prof. Dr. Kiyosei Takasu

Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)

Abstract

A Brønsted-acid-catalyzed intramolecular enantioselective SN2′ reaction was developed utilizing trichloroacetimidate  as a leaving group. The findings indicated that dual activation of the substrates is operative. This metal-free  allylic alkylation allows highly enantioselective access to 2-vinylpyrrolidines bearing various substituents.

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