• Media type: E-Article
  • Title: A Stereoselective Approach to Functionalized Cyclohexenones
  • Contributor: Meister, Anne C.; Sauter, Paul F.; Bräse, Stefan
  • imprint: Wiley, 2013
  • Published in: European Journal of Organic Chemistry
  • Language: English
  • DOI: 10.1002/ejoc.201300752
  • ISSN: 1099-0690; 1434-193X
  • Keywords: Organic Chemistry ; Physical and Theoretical Chemistry
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p>A catalytic enantioselective approach to 4‐hydroxy‐6‐methylcyclohex‐2‐enones is presented herein. The stereogenic information is generated through a copper‐catalyzed 1,4‐addition to <jats:italic>p</jats:italic>‐benzoquinone monoketal using a chiral, BINOL‐based (BINOL = 1,1′‐bi‐2‐naphthol) phosphane ligand, according to the procedure of Feringa et al. A CBS (Corey–Bakshi–Shibata) reduction of the 1,4‐adducts gave the four possible isomers in two steps and 82–97 % <jats:italic>ee</jats:italic> (enantiomeric excess), starting from commercially available 4,4‐dimethoxycyclohexa‐2,5‐dien‐1‐one (<jats:bold>7</jats:bold>).</jats:p>