ChemInform Abstract: PRODUCTION OF (+)‐(S)‐ETHYL 3‐HYDROXYBUTYRATE AND (‐)‐(R)‐ETHYL 3‐HYDROXYBUTYRATE BY MICROBIAL REDUCTION OF ETHYL ACETOACETATE

The gas-phase behavior of monocationic Ni(II) complexes that contain as building blocks optically pure BINOL derivatives and two chiral hydroxy esters is investigated by means of electrospray ionization (ESI) mass spectrometry. Upon collision-induced dissociation (CID), the complexes containing ethyl 2-hydroxypropionate (ethyl lactate) only lose the ester ligand. The complexes bearing ethyl 3-hydroxybutyrate instead either lose the ester ligands or undergo bond activation followed by elimination of the corresponding β-ketoester (ethyl acetylacetate) as revealed by deuterium labeling. Comparison of the results obtained for com- plexes with different chiralities reveals the operation of a significant stereochemical effect (SE) in the gas-phase dehydrogenation of ethyl 3-hydroxybutyrate by gaseous [(BINOLato)Ni]+ ions. Instead, no substantial differences in the CID patterns for the complexes bearing the ester-substituted BINOL derivative are found. The results provide insights into the gas-phase coordination of metal cations by BINOL derivatives and into the molecular features, which are responsible for gas-phase enantioselective processes. Additional mechanistic aspects are disclosed by exploratory calculations employing density functional theory using the B3LYP method.

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Gaseous Ni+ complexes with BINOL derivatives and chiral esters in the gas phase: an experimental and theoretical investigation

Novara

Zhang

Schröder

et al. 2009

Collect. Czech. Chem. Commun.

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ChemInform Abstract: PRODUCTION OF (+)‐(S)‐ETHYL 3‐HYDROXYBUTYRATE AND (‐)‐(R)‐ETHYL 3‐HYDROXYBUTYRATE BY MICROBIAL REDUCTION OF ETHYL ACETOACETATE

Abstract: Die Gewinnung des Hydroxybutyrats (I) aus Acetessigester in höheren Ausb. und höherer optischer Reinheit als bei den üblichen Darstellungsverfahren gelingt durch kontinuierliche Zugabe des Substrates (II) und Sucrose zu einer mit Luft versetzten Suspension von Bäckerhefe.

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Gaseous Ni+ complexes with BINOL derivatives and chiral esters in the gas phase: an experimental and theoretical investigation

Gaseous Ni+ complexes with BINOL derivatives and chiral esters in the gas phase: an experimental and theoretical investigation

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