Publication

Enantioselective Access to 1H-Isoindoles with Quaternary Stereogenic Centers by Palladium(0)-Catalyzed C-H Functionalization

Nicolai Cramer, Daria Grosheva
2018
Journal Articles

Abstract

A catalytic enantioselective method for the synthesis of chiral 1H-isoindoles bearing quaternary stereogenic centers is reported. Powered by readily accessible phosphordiamidite ligands, the presented palladium(0)-catalyzed C-H function-alization uses trifluoroacetimidoyl chlorides as electrophilic components. It delivers previously inaccessible perfluoroalky-lated 1H-isoindoles in high yields and enantioselectivities. The subsequent diastereoselective addition of nucleophiles provides access to densely substituted and sterically hindered isoindolines.

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https://infoscience.epfl.ch/entities/publication/90ca64ac-6e3f-405f-a367-dd7ce7ff1d3f

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Nicolai Cramer, Daria Grosheva
2018
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/90ca64ac-6e3f-405f-a367-dd7ce7ff1d3f

About this result

Related concepts (7)

Indole

Indole is an aromatic, heterocyclic, organic compound with the formula . It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence.

Tautomer

Tautomers (ˈtɔːtəmɚ ) are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life.

Heterocyclic compound

A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles.

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