Publication

Cobalt(III)-Catalyzed Synthesis of Chiral 1,2-Amino Alcohols by C–H Carboamidation

2025

Abstract

An efficient enantioselective synthesis of vicinal amino alcohols by C−H functionalization of pyrazolo-substituted arenes and O-allyl hydroxylamines as amino alcohol C3-synthon with built-in amidation capability is reported. The transformation is enabled by a chiral cyclopentadienyl cobalt(III) complex, providing enantioselectivities of up to 98:2 er with a broad range of substrates. The generated chiral β-amino alcohols are versatile building blocks of high synthetic value. Notably, turnover numbers of up to 52 were achieved ranging in the very top-end for asymmetric high-valent cobalt C−H functionalization catalysis.

Official source

https://infoscience.epfl.ch/entities/publication/7c0a5104-55d6-42ed-815c-5d9fec77b096

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2025

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/7c0a5104-55d6-42ed-815c-5d9fec77b096

About this result

Related concepts (24)

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

Kinetic resolution

In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer. As opposed to chiral resolution, kinetic resolution does not rely on different physical properties of diastereomeric products, but rather on the different chemical properties of the racemic starting materials.

Metal carbonyl

Metal carbonyls are coordination complexes of transition metals with carbon monoxide ligands. Metal carbonyls are useful in organic synthesis and as catalysts or catalyst precursors in homogeneous catalysis, such as hydroformylation and Reppe chemistry. In the Mond process, nickel tetracarbonyl is used to produce pure nickel. In organometallic chemistry, metal carbonyls serve as precursors for the preparation of other organometallic complexes.

Related publications (1)

Cobalt(III)-Catalyzed Synthesis of Chiral 1,2-Amino Alcohols by C–H Carboamidation

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Stereochemical effects in supramolecular self-assembly at surfaces: 1-D versus 2-D enantiomorphic ordering for PVBA and PEBA on Ag(111)