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...
Main Authors: | , , |
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Format: | Other Non-Article Part of Journal/Newspaper |
Language: | unknown |
Published: |
Taylor & Francis
2021
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Subjects: | |
Online Access: | https://dx.doi.org/10.6084/m9.figshare.15138089 https://tandf.figshare.com/articles/journal_contribution/The_absolute_configuration_of_2-bromo-2_3-dihydro-1_i_H_i_-inden-1-ols/15138089 |
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. |
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