AI Article Synopsis
- Researchers demonstrated that freshly ripened clementine mandarin can effectively reduce prochiral ketones in water, achieving high enantioselectivities (95%, 99%, and 86% ee for indanone, tetralone, and thiochromanone, respectively).
- When comparing biocatalytic and metal-catalyzed methods, chiral ruthenium catalysts also showed promising results with enantiomeric excesses over 75%, influenced by substrate and ligand types.
- Among the catalysts tested, N-aminoindanol prolinamide emerged as the most effective ligand for various ketones, and both citrus and ruthenium methods could produce different enantiomers from certain substrates.
Article Abstract
Biocatalytic reduction of prochiral ketones using freshly ripened clementine mandarin (Citrus reticulata) in aqueous medium is reported. High enantioselectivities were observed, especially for the bioreduction of indanone , tetralone , and thiochromanone with respectively 95%, 99%, and 86% enantiomeric excess (ee). Enantioselective bio- and metal-catalyzed reactions were compared. Chiral ruthenium catalysts afforded good asymmetric inductions (>75% ee) in most cases, enantiomeric excesses depending on the nature of substrate and ligand. N-aminoindanol prolinamide was revealed as the best ligand for most ketones. Interestingly, for several substrates both enantiomers could be obtained using either Citrus reticulata or ruthenium complex.
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| http://dx.doi.org/10.1002/chir.22413 | DOI Listing |
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