Synthesis of quaternary carbon centers via hydroformylation

J Am Chem Soc. 2010 Sep 1;132(34):11841-3. doi: 10.1021/ja1036226.

Abstract

The application of hydroformylation to the synthesis of quaternary carbon centers is reported. The synthesis of the highly substituted carbon is achieved by applying a catalytic amount of 1. Ligand 1 serves as a catalytic directing group by covalently and reversibly binding to both the substrate and catalyst. The intramolecular nature of the directing group strategy accelerates the hydroformylation reaction such that the reaction is performed at mild temperatures (35-55 degrees C) and with excellent regioselectivity (b:l > 94:6).

Publication types

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

MeSH terms

  • Acetals / chemical synthesis*
  • Acetals / chemistry
  • Alcohols / chemistry*
  • Alkenes / chemistry*
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Cyclization
  • Ligands
  • Molecular Structure
  • Stereoisomerism
  • Temperature

Substances

  • Acetals
  • Alcohols
  • Alkenes
  • Carboxylic Acids
  • Ligands