Combining lipase-catalyzed enantiomer-selective acylation with fluorous phase labeling: a new method for the resolution of racemic alcohols.
Lipase-catalyzed acylation of racemic alcohols with a highly fluorinated acyl donor allows their kinetic resolution accompanied by the simultaneous enantiomer-selective fluorous phase labeling. Both the tagged and the untagged enantiomer can be separated without chromatography by a very efficient partition between a fluorous and an organic phase. The method has been successfully applied to the resolution of typically racemic secondary alcohols of low molecular weight. The fluorous label can be recovered quantitatively.
Hungerhoff
Benno
B
ASCA GmbH Angewandte Synthesechemie Adlershof, Richard-Willstätter-Strasse 12, D-12489 Berlin, Germany.
Sonnenschein
Helmut
H
Theil
Fritz
F
D000215:Acylation; D000438:Alcohols / Q000737:chemistry*; D016956:Burkholderia cepacia / Q000201:enzymology*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D000438:Alcohols; D006845:Hydrocarbons, Fluorinated; D014753:Vinyl Compounds; D008049:Lipase; C011566:vinyl acetate