Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

Abstract

The main purpose of this work was to discover the way to obtain pure enantiomers of indan-1-ol. The subject of the study was the ability of the plant enzyme system to reduce the carbonyl group of indan-1-one, as well as to oxidize the hydroxyl group of racemic indan-1-ol. Locally available fruit and vegetables were selected for stereoselective biotransformation. During the reduction, mainly alcohol of the S-(+)-configuration with a high enantiomeric excess (ee = 99%) was obtained. The opposite enantiomer was obtained in bioreduction with the apple and parsley. Racemic indan-1-ol was oxidized by all catalysts. The best result was obtained for the Jerusalem artichoke: Over 50% conversion was observed after 1 h, and the enantiomeric excess of unreacted R-(–)-indan1-ol was 100%.

Plant-Mediated Enantioselective Transformation of Indan-1-one and Indan-1-ol. Part 2

“…Recently, we have developed an effective biotechnological method for obtaining R -(−)-indan-1-ol using ground Jerusalem artichoke pulp, where after 1 h over 50% conversion has been observed and the enantiomeric excess of unreacted R -alcohol was 100% [11]. During this transformation, highly stereo-selective oxidation of racemic alcohol was observed.…”

“…Plant cell cultures have been employed for the enantioselective transformation of xenobiotics and have been shown to be good biochemical systems for enantioselective synthesis. Among the used cell and roots cultures, carrots seem to be very efficient for asymmetric reduction of prochiral ketones, not only in the form of crushed pulp [11,12,13,14,15,16,17,18,19,20,21,22] but also cell [17,23,24,25,26] and hairy roots cultures [27]. Based on literature date, [11,28,29,30,31] only few biocatalytic methods were used to obtain indan-1-ol enantiomers.…”

Boosting Solvent-Free Aerobic Oxidation of Benzylic Compounds into Ketones over Au-Pd Nanoparticles Supported by Porous Carbon

“…Indane, as a representative benzylic compounds, is present in many vital biological and medicinal systems [24]. Indanone, as the main product of indane oxidation, is an important intermediate for a variety of fine chemicals, such as pharmaceuticals, agrochemicals, and dyes [25]. Monometallic Au or Pd nanoparticles supported catalysts that have exhibited good catalytic activity for the controlled indane oxidation.…”