Tetrahydrobenzochromene Synthesis Enabled by a Deconjugative Alkylation/Tsuji-Saegusa-Ito Oxidation on Knoevenagel Adducts

Org Lett. 2018 Aug 3;20(15):4566-4570. doi: 10.1021/acs.orglett.8b01857. Epub 2018 Jul 16.

Abstract

A modular and practical route to versatile cyano-1,3-dienes by a sequence involving deconjugative alkylation and "Tsuji-Saegusa-Ito oxidation" is reported. In this letter, the versatility of the products is also explored, including a route to benzochromene scaffolds common to many natural products.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry
  • Alkylation
  • Benzopyrans / chemical synthesis*
  • Catalysis
  • Isomerism
  • Molecular Structure
  • Nitriles / chemistry
  • Organometallic Compounds / chemistry
  • Oxidation-Reduction
  • Palladium / chemistry

Substances

  • Alkadienes
  • Benzopyrans
  • Nitriles
  • Organometallic Compounds
  • Palladium