Optically active trans-2-aminocyclopentanols: chemoenzymatic preparation and application as chiral ligands.
Optically active trans-2-(N,N-dialkylamino)cyclopentanols and their acetates derivatives were obtained with very good chemical yields and enantiomeric excesses (95->/=99%), through a chemoenzymatic methodology based on the lipase-catalyzed acylation of the hydroxyl group. The utility of these compounds was shown by the preparation of the cyclopentylic analog of vesamicol and by their use as ligands in the enantioselective addition of diethylzinc to benzaldehyde.
González-Sabín
Javier
J
Departamento de Química Orgánica e Inorgánica e Instituto de Biotecnología, Universidad de Oviedo, Oviedo, Spain.
Gotor
Vicente
V
Rebolledo
Francisca
F
D000085:Acetates / Q000737:chemistry* / Q000528:radiation effects; D016956:Burkholderia cepacia / Q000201:enzymology*; D002384:Catalysis; D004800:Enzymes, Immobilized / Q000737:chemistry; D004951:Esterification; D007536:Isomerism; D008027:Light; D008049:Lipase / Q000737:chemistry*; D000439:Pentanols / Q000737:chemistry* / Q000528:radiation effects
D000085:Acetates; D004800:Enzymes, Immobilized; D000439:Pentanols; D008049:Lipase