Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes

Angew Chem Int Ed Engl. 2018 Jan 26;57(5):1390-1393. doi: 10.1002/anie.201712015. Epub 2018 Jan 4.

Abstract

An inside job: Enantioselective phthalide synthesis was achieved through internal redox allylation of o-phthalaldehydes. Oxidative esterification is balanced by reductive carbonyl addition to achieve an overall redox-neutral process. This method enabled formal syntheses of ent-spirolaxine methyl ether and CJ-12,954.

Keywords: C−C Bond Formation; Homogeneous Catalysis; Hydrogen Transfer; Iridium; asymmetric catalysis.

Publication types

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

MeSH terms

  • Benzofurans / chemistry*
  • Catalysis
  • Esterification
  • Hydrogenation
  • Iridium / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism
  • o-Phthalaldehyde / chemistry*

Substances

  • Benzofurans
  • Iridium
  • o-Phthalaldehyde
  • phthalide