Synlett
DOI: 10.1055/s-0036-1588469
cluster
© Georg Thieme Verlag Stuttgart · New York

Reactions of Nitrosobenzenes with Cyclobutanones by Activation with a Lewis Acid

Yusuke Shima, Emiko Igarashi, Tomoyuki Yoshimura, Jun-ichi Matsuo*
  • Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan   Email: jimatsuo@p.kanazawa-u.ac.jp
This work was supported by JSPS KAKENHI Grant Number 15K07855.
Further Information

Publication History

Received: 26 April 2017

Accepted after revision: 23 May 2017

Publication Date:
05 July 2017 (eFirst)

Published as part of the Cluster C–C Activation
Dedicated to Professor Teruaki Mukaiyama in celebration of his 90th birthday

Abstract

Formal [4+2] cycloaddition between 3-ethoxy-2-alkylcyclobutanones and nitrosobenzene proceeded by activation with Me3SiOTf to afford 6-alkyl-2-phenyl-2H-1,2-oxazin-5(6H)-one by regioselective cleavage of the more substituted C2–C3 bond of the cyclobutanone ring. On the other hand, reactions of 3-phenylcyclobutanones and 2-benzyloxycyclobutanone with nitrosobenzene gave γ,δ-unsaturated and cyclic hydroxamic acid derivatives, respectively, by cleavage of a cyclobutanone C1–C2 bond.

Supporting Information