Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric SN 2' Reaction

Yusuke Kuroda; Shingo Harada; Akinori Oonishi; Yousuke Yamaoka; Ken-Ichi Yamada; Kiyosei Takasu

doi:10.1002/anie.201502831

Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric SN 2' Reaction

Angew Chem Int Ed Engl. 2015 Jul 6;54(28):8263-6. doi: 10.1002/anie.201502831. Epub 2015 May 28.

Authors

Yusuke Kuroda¹, Shingo Harada¹, Akinori Oonishi¹, Yousuke Yamaoka¹, Ken-Ichi Yamada², Kiyosei Takasu³

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan).
² Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan). yamak@pharm.kyoto-u.ac.jp.
³ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan). kay-t@pharm.kyoto-u.ac.jp.

PMID: 26016987
DOI: 10.1002/anie.201502831

Abstract

A Brønsted-acid-catalyzed intramolecular enantioselective SN 2' 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.

Keywords: asymmetric catalysis; nucleophilic substitution; organocatalysis; pyrrolidines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemistry*
Catalysis
Molecular Structure
Pyrrolidines / chemistry*
Stereoisomerism

Substances

Allyl Compounds
Pyrrolidines