884845-06-1Relevant articles and documents
Asymmetric reduction of perfluoroalkyl ketones with chiral lithium alkoxides
Sokeirik, Yasser Samir,Sato, Kazuyuki,Omote, Masaaki,Ando, Akira,Kumadaki, Itsumaro
, p. 2821 - 2824 (2007/10/03)
Reduction of perfluoroalkyl ketones with chiral lithium alkoxides gave chiral α-perfluoroalkyl alcohols in high enantiomeric excesses. Interestingly, reaction of 2,2,2-trifluoroacetophenone (1) with lithium (S)-1-phenylethoxide (2) gave (S)-2,2,2-trifluoro-1-phenylethanol (3), while the same reaction of perfluorooctan-1-one (7) with 2 gave (R)-1H-1- phenylperfluorooctanol (8). Based on the speculation of mechanism, the order of steric effects on this reaction is estimated as C7F15 > substituted phenyl > CF3.