158529-97-6Relevant articles and documents
Microwave-promoted lipase-catalyzed reactions
Lin, Gialih,Lin, Wen-Yuan
, p. 4333 - 4336 (1998)
Lipase from porcine pancreas is demonstrated to catalyze acylation reactions in organic media under microwave irradiation. Reaction rates and enantioselectivities are significantly enhanced 1-14 and 3-9 fold, respectively.
Removal of the acyl donor residue allows the use of simple alkyl esters as acyl donors for the dynamic kinetic resolution of secondary alcohols
Verzijl, Gerard K.M.,De Vries, Johannes G.,Broxterman, Quirinus B.
, p. 1603 - 1610 (2007/10/03)
The dynamic kinetic resolution of secondary alcohols using a lipase and a ruthenium catalyst as developed by Baeckvall required some improvements to make it suitable for its use in an industrial process. The use of p-chlorophenyl acetate as acyl donor is not desirable in view of the toxicity of the side product. We herein report that simple alkyl esters can be used as acyl donors if the alcohol or ketone residue formed during the enzymatic acylation is continuously removed during the reaction. The addition of a ketone speeds up the racemisation process and allowed us to reduce the amounts of enzyme and ruthenium catalyst. The scope of this method was explored and a suitable range of acyl donors found. Various benzylic and aliphatic alcohols were reacted using isopropyl butyrate or methyl phenylacetate as acyl donor and in most cases the ester was isolated in >95% yield and 99% ee. Furthermore, it was demonstrated that the alcohol by-products of the enzymatic resolution could be used as the hydrogen source in the asymmetric reductive transesterification of ketones.
Multiple Enantioselection by an Enzyme-Catalyzed Transacylation Reaction
Lin, Gialih,Chen, Show-Jane,Sun, Hwey-Lin
, p. 459 - 466 (2007/10/03)
Multiply enantioselective enzyme-catalyzed transacylation reactions are described.Two instances of triply enantioselective enzyme-catalyzed transacylations are 1) the reaction of rac-1-indanol with rac-1,1'-bi-2-naphthyl-2,2'-dibutyrate to afford (S)-1-indanol, (R)-1-indanylacetate, (S)-1,1'-bi-2-naphthyl-2,2'-diol, and (R)-1,1'-bi-2-naphthyl-2,2'-dibutyrate and 2) the reaction of rac-1-indanol with rac-2,2'-bis(butyroxymethyl)biphenyl to afford (S)-1-indanol, (R)-1-indanylbutyrate, (S)-2,2'-biphenyldimethanol, and (R)-2,2'-bis(butyroxy-methyl)biphenyl.Doubly enantioselective enzyme-catalyzed transacylations are described according to two instances: 1) the reaction of rac-1-indanol with rac-1,1'-bi-2-naphthyl-2-ol-2'-butyrate afforded (S)-1-indanol, (R)-1-indanylacetate, (S)-1,1'-bi-2-naphthyl-2,2'-diol, and (R)-1,1'-bi-2-naphthyl-2-ol-2'-butyrate, and 2) the reaction of rac-1-indanol with 1,3,5-O-methylidne-2,4,6-tri-O-butyrate-myo-inositol to afford (S)-1-indanol, (R)-1-indanylbutyrate, and 1,3,5-O-methylidne-2,6-di-O-butyrate-myo-inositol.Multiply enantioselective enzyme-catalyzed reactions have a merit of the enhancement of enantiomeric excess over singly enantioselective ones. - Key Words Enzyme in organic synthesis; Kinetic resolution; Lipase.
