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

All four possible stereoisomers of cis- and trans-2-bromo-2,3-dihydro-1 H -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 r...

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Bibliographic Details
Main Authors: Dmitry V. Prysiazhnuk (11250911), Eduard B. Rusanov (1446721), Oleg I. Kolodiazhnyi (8780009)
Format: Other Non-Article Part of Journal/Newspaper
Language:unknown
Published: 2021
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Online Access:https://doi.org/10.6084/m9.figshare.15138089.v1
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Summary:All four possible stereoisomers of cis- and trans-2-bromo-2,3-dihydro-1 H -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-1 H -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-1 H -inden-1-ols were established.