Synlett
DOI: 10.1055/s-0036-1589091
letter
© Georg Thieme Verlag Stuttgart · New York

Trapping of Hexadehydro-Diels–Alder Benzynes with Exocyclic, Conjugated Enals as a Route to Fused Spirocyclic Benzopyran Motifs

Tao Wang, Christian J. Oswood, Thomas R. Hoye*
  • Department of Chemistry, University of Minnesota, 207 Pleasant St., SE, Minneapolis, Minnesota 55455, USA   Email: hoye@umn.edu
Financial support for these studies was provided by the National Institute of General Medical Sciences (R01 GM108762) of the National Institutes of Health. NMR data were recorded, in part, using an instrument purchased through a NIH Shared Instrumentation Grant (S10OD011952).
Further Information

Publication History

Received: 13 June 2017

Accepted after revision: 11 July 2017

Publication Date:
22 August 2017 (eFirst)

Dedicated with very best wishes to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

Exocyclic, conjugated enals react with benzynes generated by heating various triyne-containing substrates to produce spirocyclic benzopyran derivatives. These products are consistent with a mechanistic sequence that involves initial net [2+2] cycloaddition of the benzyne and aldehyde followed by 4π-electrocyclic ring opening and 6π ring closing.

Supporting Information