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Bienzymatic Dynamic Kinetic Resolution of Secondary Alcohols by Esterification/Racemization in Water.
Angew Chem Int Ed Engl
November 2024
Laboratory of Biocatalysis and Biotransformation, Department of Drugs Technology and Biotechnology, Faculty of Chemistry, Warsaw University of Technology, Koszykowa 75, 00-662, Warsaw, Poland.
Dynamic kinetic resolution (DKR) is a key method used to prepare optically pure compounds in 100 % theoretical yield starting from racemic substrates by combining the interconversion of substrate enantiomers with an enantioselective transformation. Various chemoenzymatic DKR approaches have been developed to deracemize secondary alcohols, typically requiring an organic solvent to facilitate enantioselective acylation, primarily catalyzed by lipases, alongside racemization mediated by an achiral, non-enzymatic catalyst. Achieving both steps in an aqueous solution remained elusive.
View Article and Find Full Text PDFOrganic Synthesis Away from Equilibrium: Contrathermodynamic Transformations Enabled by Excited-State Electron Transfer.
Acc Chem Res
July 2024
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
ConspectusChemists have long been inspired by biological photosynthesis, wherein a series of excited-state electron transfer (ET) events facilitate the conversion of low energy starting materials such as HO and CO into higher energy products in the form of carbohydrates and O. While this model for utilizing light-driven charge transfer to drive catalytic reactions thermodynamically "uphill" has been extensively adapted for small molecule activation, molecular machines, photoswitches, and solar fuel chemistry, its application in organic synthesis has been less systematically developed. However, the potential benefits of these approaches are significant, both in enabling transformations that cannot be readily achieved using conventional thermal chemistry and in accessing distinct selectivity regimes that are uniquely enabled by excited-state mechanisms.
View Article and Find Full Text PDFNonlinear Effects in Asymmetric Catalysis by Design: Concept, Synthesis, and Applications.
Acc Chem Res
December 2022
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München, Germany.
Asymmetric synthesis constitutes a key technology for the preparation of enantiomerically pure compounds as well as for the selective control of individual stereocenters in the synthesis of complex compounds. It is thus of extraordinary importance for the synthesis of chiral drugs, dietary supplements, flavors, and fragrances, as well as novel materials with tunable and reconfigurable chiroptical properties or the assembly of complex natural products. Typically, enantiomerically pure catalysts are used for this purpose.
View Article and Find Full Text PDFThe unexpected dominance of secondary over primary nucleation.
Faraday Discuss
July 2022
Laboratoire Sciences et Méthodes Séparatives, Université de Rouen Normandie, Place Emile Blondel, 76821 Mont Saint Aignan Cedex, France.
It is still a challenge to control the formation of particles in industrial crystallization processes. In such processes, new crystals can be generated either by primary or secondary nucleation. While in continuous stirred tank crystallization processes, secondary nucleation is thought to occur due to the shear or attrition of already present larger crystals; in antisolvent crystallization processes, where mixing at the inlets locally causes high supersaturations, primary nucleation is understood to be the main mechanism.
View Article and Find Full Text PDFVisible-Light-Driven Catalytic Deracemization of Secondary Alcohols.
Angew Chem Int Ed Engl
October 2021
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Poly-technique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne, 1015, Switzerland.
Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols which are important synthetic intermediates and end products for many industries. Driven by visible light only, this method is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation.
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