145167-51-7Relevant academic research and scientific papers
Enzymatic process for the stereoselective preparation of a hetero-bicyclic alcohol enantiomer
-
, (2008/06/13)
The invention relates to an enzymatic process for the stereoselective preparation of a hetero-bicyclic alcohol enantiomer, characterized in that a substantially pure enantiomer of the general formula wherein X is O, S, NH, N-(C1-C4)alkyl or CH2;, Y1, Y2 and Y3 are each independently hydrogen or substituents selected from halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, nitro and cyano;, the NO2 substituent is attached to the bicyclic ring system in the 5- or 7-position; and, the C*-atom has either the R or the S configuration;, is prepared from its corresponding alcohol racemate by the following successive reaction steps: (1) stereoselective esterification, (2) separation of the alcohol from the ester produced, (3) hydrolysis of said ester to produce the corresponding alcohol enantiomer, and (4) conversion of said alcohol enantiomer into the starting racemate under basic conditions in order to allow its reuse. The invenion also relates to a substantially pure alcohol enantiomer of formula I, to the use of said enantiomer for the preparation of a pharmacologically active piperazine derivative, and to substantially pure enantiomeric intermediates.
The synthesis of (+)- and (-)-flesinoxan: Application of enzymatic resolution methodology
Ennis,Ghazal
, p. 6287 - 6290 (2007/10/02)
The synthesis of (±)-flesinoxan was carried out in seven steps starting from catechol. An enzymatic resolution was utilized to prepare each enantiomer. Based upon the known preferences of the enzyme system used, we have assigned the (R)-configuration to the (+)-flesinoxan isomer.
