Chemoenzymatic synthesis of both enantiomers of 3-hydroxy-2,2-dimethylcyclohexanone.
The stereoselective acetylation of meso-2,2-dimethyl-1,3-cyclohexanediol by vinyl acetate in the presence of three lipases gave the (1R,3S)-monoester in high enantiomeric excess (ee > or = 98%). The hydrolysis of the corresponding meso-diacetate in the presence of Candida antarctica lipase in phosphate buffer provided the opposite enantiomer. Optically active monoacetates were converted to both enantiomers of 3-hydroxy-2,2-dimethylcyclohexanone, a versatile chiral building block.
Chênevert
Robert
R
Département de Chimie, CREFSIP, Faculté des Sciences et de Genie, Université Laval, Québec (QC), Canada G1K 7P4. robert.chenevert@chm.ulaval.ca
Lévesque
Carine
C
Morin
Pierre
P
D000818:Animals; D001234:Aspergillus niger / Q000201:enzymology; D002021:Buffers; D016956:Burkholderia cepacia / Q000201:enzymology; D002175:Candida / Q000201:enzymology; D002625:Chemistry, Organic / Q000379:methods*; D003512:Cyclohexanones / Q000737:chemistry*; D004952:Esters; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry*; D008956:Models, Chemical; D010100:Oxygen / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D013237:Stereoisomerism; D013552:Swine
D002021:Buffers; D003512:Cyclohexanones; D004952:Esters; D010710:Phosphates; D008049:Lipase; D010100:Oxygen