Title of article
Asymmetric reduction of perfluoroalkyl ketones with chiral lithium alkoxides
Author/Authors
Y.S. Sokeirik and H. Safwat، نويسنده , , Yasser Samir and Sato، نويسنده , , Kazuyuki and Omote، نويسنده , , Masaaki and Ando، نويسنده , , Akira and Kumadaki، نويسنده , , Itsumaro، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2006
Pages
4
From page
2821
To page
2824
Abstract
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.
Keywords
?-(Perfluoroalkyl)carbinol , trifluoroacetophenone , 1-Phenylethanol , Steric effect , asymmetric reduction , Perfluoroalkyl ketone , Chiral transfer , lithium alkoxide
Journal title
Tetrahedron Letters
Serial Year
2006
Journal title
Tetrahedron Letters
Record number
1849714
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