Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts

Shota Nagasawa; Yusuke Sasano; Yoshiharu Iwabuchi

doi:10.1002/anie.201607752

Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts

Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13189-13194. doi: 10.1002/anie.201607752.

Authors

Shota Nagasawa¹, Yusuke Sasano¹, Yoshiharu Iwabuchi²

Affiliations

¹ Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
² Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan. y-iwabuchi@m.tohoku.ac.jp.

PMID: 27650040
DOI: 10.1002/anie.201607752

Abstract

Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.

Keywords: alkenes; dehydrogenation; ene reaction; regioselectivity; synthetic methods.

Publication types

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