Chemoselective aromatic C-H insertion of α-diazo-β-ketoesters catalyzed by dirhodium(II) carboxylates

Org Lett. 2012 Jan 6;14(1):238-40. doi: 10.1021/ol202968z. Epub 2011 Nov 30.

Abstract

The ability of α-diazo-β-ketoesters bearing a substituent on the benzylic position to undergo aromatic C-H insertion is described. Good to excellent yields of the aromatic C-H insertion products were observed with Rh(2)(tpa)(4) or Rh(2)(esp)(2) catalysts. This is an attractive strategy to prepare tetralins carrying a methyl group on the benzylic position, a structural motif found in several types of natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry*
  • Carbon / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Esters / chemistry*
  • Hydrogen / chemistry*
  • Molecular Structure
  • Rhodium / chemistry*

Substances

  • Azo Compounds
  • Carboxylic Acids
  • Esters
  • Carbon
  • Hydrogen
  • Rhodium