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Synthesis of Chiral Bifunctional (Thio)Urea N-Heterocyclic Carbenes

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Jérôme Waser, Jonathan Brand, Jose Ignacio Osuna Siles
2010

Résumé

The rapid and modular synthesis of the first bifunctional N-heterocyclic carbenes bearing a (thio)urea moiety as H-bond donor group was reported. Different analogues could be accessed in seven steps from cheap (S)-pyroglutamic acid in good overall yields (14-30%). The synthesized carbenes were active catalysts in the benzoin reaction.

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https://infoscience.epfl.ch/entities/publication/2b7eaaad-42ea-4dcb-95df-b34b606384fe

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Concepts associés (6)

Persistent carbene

A persistent carbene (also known as stable carbene) is a type of carbene demonstrating particular stability. The best-known examples and by far largest subgroup are the N-heterocyclic carbenes (NHC) (sometimes called Arduengo carbenes), for example diaminocarbenes with the general formula (R2N)2C:, where the four R moieties are typically alkyl and aryl groups. The groups can be linked to give heterocyclic carbenes, such as those derived from imidazole, imidazoline, thiazole or triazole.

Transition metal carbene complex

A transition metal carbene complex is an organometallic compound featuring a divalent organic ligand. The divalent organic ligand coordinated to the metal center is called a carbene. Carbene complexes for almost all transition metals have been reported. Many methods for synthesizing them and reactions utilizing them have been reported. The term carbene ligand is a formalism since many are not derived from carbenes and almost none exhibit the reactivity characteristic of carbenes.

Catalyseur de Grubbs

Un catalyseur de Grubbs est un complexe métal de transition-carbène qui doit son nom à Robert Grubbs, le premier à les avoir synthétisés. Il existe plusieurs générations de ce catalyseur (les deux premières sont détaillées à droite). Contrairement aux autres catalyseurs utilisés dans la métathèse des oléfines, le catalyseur de Grubbs tolère la présence d'autres groupements fonctionnels et peut être utilisé dans de nombreux solvants. C'est pour cela que ce catalyseur est abondamment employé.

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