Abstract

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.

摘要

顺式和反式 2-bromo-2,3-dihydro-1 H -inden-1-ols 的所有四种可能的立体异构体都被合成，它们是生物活性化合物合成中的重要中间体，并通过酶促研究了它们的构型。通过应用 Kazlauskas 规则、X 射线衍射分析以及使用 NOE-NMR 和 Karplus 方程进行 NMR 的动力学分辨率。生物催化动力学酯交换用于拆分外消旋物。脂肪酶洋葱伯克霍尔德菌和南极念珠菌 B (Novozyme 435) 可有效用作生物催化剂，用于 2-bromo-2,3-dihydro-1 H -inden-1-ols 与乙酸异丙酯的生物催化酯化。2-bromo-2,3-dihydro-1 H的(S,S)-、(R,R)-、(S,R)-和(R,S)-立体异构体的绝对构型-inden-1-ols 成立。