1053243-53-0Relevant academic research and scientific papers
Bicyclo[2.2.2]octane-derived chiral ligands-synthesis and application of BODOLs in the asymmetric reduction of acetophenone with catecholborane
Friberg, Annika,Sarvary, Ian,Wendt, Ola F.,Frejd, Torbjoern
, p. 1765 - 1777 (2008/12/23)
An improved synthetic route to the bicyclo[2.2.2]octane-2,6-diol ligands (2,6-BODOLs) allowed an increased structural variation of the ligand side-arm. The addition of aromatic or vinylic Grignard reagents to hydroxyketone 1 was highly selective and ligands 3f-3l were isolated in 84-97% yield. The addition of alkyl Grignard reagents containing β-hydrogens resulted in lower yields (13-71%) due to competing ketone reduction. A number of 2,5-BODOLs were synthesized using a similar methodology. The ligands, together with Ti(OiPr)4, were tested in the asymmetric reduction of acetophenone with catecholborane (up to 98% ee). 1-Naphthyl-BODOL 3i was employed as an allylboration reagent to benzaldehyde together with Sc(OTf)3, resulting in (1S)-1-phenyl-3-buten-1-ol in 80% ee.
