Enantioselective Isomerization of Primary Allylic Alcohols into Chiral Aldehydes with the tol‐binap/dbapen/Ruthenium(II) Catalyst

• DOI: 10.1002/anie.201303423
• Publication Date: 2013-06-26T14:29:50Z
• Authors: Noriyoshi Arai; Keisuke Sato; Keita Azuma; Takeshi Ohkuma
• Keywords: BINAP

Efficient isomerization: The title reaction was catalyzed by the [RuCl2{(S)-tol-binap}{(R)-dbapen}]/KOH system in ethanol at 25 °C (see scheme). A series of E- and Z-configured aromatic aliphatic allylic alcohols, including a simple primary alkyl-substituted compound (E)-3-methyl-2-hepten-1-ol, were transformed into chiral aldehydes with least 99 % ee. dbapen = 2-dibutylamino-1-phenylethylamine, tol-binap 2,2'-bis(di-4-tolylphosphanyl)-1,1'-binaphthyl.