Synlett
DOI: 10.1055/s-0036-1589049
letter
© Georg Thieme Verlag Stuttgart · New York

A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation–Ring-Expansion Approach to Substituted Azepanes

Scott M. Thullena, b, David M. Rubushb, c, Tomislav Rovis*a, b
  • aDepartment of Chemistry, Columbia University, New York, NY 10027, USA   Email: tr2504@columbia.edu
  • bDepartment of Chemistry, Colorado State University, Fort Collins, CO 80523, USA
  • cCurrent Address: Department of Chemistry, Benedictine University, Lisle, IL 60532, USA
We thank NIGMS for support (GM80442)
Further Information

Publication History

Received: 08 March 2017

Accepted after revision: 10 May 2017

Publication Date:
29 June 2017 (eFirst)

Dedicated to our friend and colleague Victor Snieckus on the occasion of his 80th birthday.

Abstract

Seven-membered nitrogen-containing heterocycles are considerably underrepresented in the literature compared to their five- and six-membered analogues. Herein, we report a relatively understudied photochemical rearrangement of N-vinylpyrrolidinones to azepin-4-ones in good yields. This transformation allows for the conversion of readily available pyrrolidinones and aldehydes to densely functionalized azepane derivatives in a facile two-step procedure.

Supporting Information