Combining Lipase-Catalyzed Enantiomer-Selective Acylation with Fluorous Phase Labeling: A New Method for the Resolution of Racemic Alcohols
Benno Hungerhoff, Helmut Sonnenschein and Fritz Theil*
*ASCA GmbH Angewandte Synthesechemie Adlershof, Richard-Willstätter-Strasse
12, D12489 Berlin, Germany, Email: theil
asca-berlin.de
B. Hungerhoff, H. Sonnenschein, F. Theil, J. Org. Chem, 2002, 67, 1781-1785.
DOI: 10.1021/jo010767p
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Abstract
Lipase-catalyzed acylation of racemic alcohols with a highly fluorinated acyl donor allows their kinetic resolution and a subsequent, efficient partition of both the tagged and untagged enantiomer between a fluorous and an organic phase. The method has been successfully applied to the resolution of secondary alcohols of low molecular weight. The fluorous label can be recovered quantitatively.
Key Words
FPOS, Fluorous Phase, Kinetic Resolution, Transesterification, Enantioselective Acylation
ID: J42-Y2002-490
