The absolute configuration of 2-bromo-2,3-dihydro-1H-inden-1-ols

All four possible stereoisomers of cis- and trans-2-bromo-2,3-dihydro-1H-inden-1-ols, which are important intermediates in the synthesis of biologically active compounds, were synthesized and their configurations were studied by enzymatic kinetic resolution with the application of the Kazlauskas rule, X-ray diffraction analysis, as well as NMR using NOE-NMR and Karplus equation. Biocatalytic kinetic trans-esterification was used for resolution of racemates. Lipases Burkholderia cepacia and Candida Antarctica B (Novozyme 435) were effective as biocatalysts for biocatalytic esterification of 2-bromo-2,3-dihydro-1H-inden-1-ols with isopropylidene acetate. The absolute configurations of (S,S)-, (R,R)-, (S,R)- and (R,S)-stereoisomers of 2-bromo-2,3-dihydro-1H-inden-1-ols were established.

Automated summary

All four possible stereoisomers of cis- and trans-2-bromo-2,3-dihydro-1H-inden-1-ols were successfully synthesized and studied using enzymatic kinetic resolution. The absolute configurations of these stereoisomers were established through a combination of methods including X-ray diffraction analysis and NMR. Biocatalytic kinetic trans-esterification was employed for resolution of racemates.