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Combining biocatalytic oxyfunctionalisation and organocatalytic aldol reaction to access chiral β-hydroxy ketones

Wang, Yutong; Domestici, Chiara; Teetz, Niklas 1; Holtmann, Dirk 1; Alcalde, Miguel; Wang, Mengfan; Qi, Wei; Zhang, Wuyuan; Hollmann, Frank
1 Karlsruher Institut für Technologie (KIT)

Abstract:

This study explores a chemoenzymatic cascade to synthesise chiral β-hydroxy ketones by integrating the selective oxyfunctionalisation capabilities of peroxygenases with the carbon-carbon bond-forming progress of organocatalysts. Initial results with simple organocatalysts demonstrated poor performance due to mutual inactivation of the biocatalyst and organocatalyst. However, the use of more complex prolinamide derivatives improved the reaction efficiency and enantioselectivity, enabling a one-pot, one-step synthesis process. This methodology was further optimised to produce high yields of enantiomerically pure aldol products and was shown to be extendable to other substituted toluenes and aldol donors.


Verlagsausgabe §
DOI: 10.5445/IR/1000174444
Veröffentlicht am 23.09.2024
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Bio- und Lebensmitteltechnik (BLT)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 12.2024
Sprache Englisch
Identifikator ISSN: 2468-8231, 2468-8274
KITopen-ID: 1000174444
Erschienen in Molecular Catalysis
Verlag Elsevier
Band 569
Seiten 114515
Vorab online veröffentlicht am 05.09.2024
Nachgewiesen in Dimensions
Web of Science
Scopus
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