Regioselective derivatizations of a tribrominated atropisomeric benzamide scaffold

Org Lett. 2015 Feb 6;17(3):580-3. doi: 10.1021/ol503593y. Epub 2015 Jan 12.

Abstract

The enantioselective synthesis of atropisomeric, tribrominated benzamides and subsequent regioselective transformations to afford derivatized, axially chiral molecules is reported. The enantioenriched tribromides were carried through sequential Pd-catalyzed cross-coupling and lithium-halogen exchange with high regioselectivity and enantioretention. A variety of complexity-generation functional group installations were performed to create a library of homochiral benzamides. The potential utility of these molecules is demonstrated by using a phosphino benzamide derivative as an asymmetric ligand in a Pd-catalyzed allylic alkylation.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkylation
  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Brominated / chemical synthesis*
  • Hydrocarbons, Brominated / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Benzamides
  • Hydrocarbons, Brominated
  • Palladium