Chiral tertiary 2-furyl alcohols: diversified key intermediates to bioactive compounds. Their enantioselective synthesis via (2-furyl)aluminium addition to ketones catalyzed by a titanium catalyst of (S)-BINOL

Chem Commun (Camb). 2008 May 28:(20):2343-5. doi: 10.1039/b802441c. Epub 2008 Apr 17.

Abstract

Novel asymmetric 2-furyl additions of (2-furyl)AlEt(2)(THF) to aromatic ketones and one alpha,beta-unsaturated ketone catalyzed by a titanium catalyst of 10-20 mol% (S)-BINOL are reported to furnish tertiary furyl alcohols in good to excellent enantioselectivities of 87-93% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aluminum / chemistry*
  • Catalysis
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Ketones / chemistry*
  • Naphthols / chemistry*
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Alcohols
  • BINOL, naphthol
  • Furans
  • Ketones
  • Naphthols
  • Organometallic Compounds
  • Aluminum
  • Titanium