3,3'-dipyridyl BINOL ligands. Synthesis and application in enantioselective addition of Et2Zn to aldehydes

Org Lett. 2007 Oct 25;9(22):4403-6. doi: 10.1021/ol071276f. Epub 2007 Sep 28.

Abstract

3,3'-di(2-pyridyl) BINOLs (4), prepared in three steps from commercial substances by a combined directed ortho metalation-Negishi cross-coupling protocol, constitute new members of the BINOL ligand family. They are among the most selective, general ligands, providing equal or greater stereoselectivities in the Et2Zn addition to benzaldehydes and cinnamaldehydes (Table 3) than any single BINOL ligand reported to date.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Naphthols / chemistry*

Substances

  • Aldehydes
  • BINOL, naphthol
  • Ligands
  • Naphthols