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

• Main Authors: Prysiazhnuk, Dmitry V., Rusanov, Eduard B., Kolodiazhnyi, Oleg I.
• Format: Other Non-Article Part of Journal/Newspaper
• Language: unknown
• Published: Taylor & Francis 2021
• Subjects: Biochemistry; Microbiology; FOS Biological sciences; Genetics; 39999 Chemical Sciences not elsewhere classified; FOS Chemical sciences; Ecology; Sociology; FOS Sociology; 69999 Biological Sciences not elsewhere classified; Developmental Biology; Plant Biology; Antarc*; Antarctica
• 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

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.