The Ritter reaction is a method of choice for the production of amides, which are versatile intermediates in organic synthesis and compounds of interest in natural product synthesis. Recent efforts have been directed towards the development of catalytic versions for the development of more eco‐friendly synthetic routes to amides. This review summarizes the recent progress in this area and covers new applications in the field of Ritter‐type and multicomponent reactions.
Cobalt, the catalyst of choice: The diastereoselective cobalt-catalyzed cross-coupling of 1-bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)(3)]/tmeda (acac = acetylacetonate, tmeda = N,N'-tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1-3:1.
Cheap and safe: An iron‐catalyzed cross‐coupling reaction between alkyl halides and alkenyl Grignard reagents is described. This CC bond coupling reaction is promoted by the cheap and nontoxic FeCl3 and displays good tolerance against various functional groups.
The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.
[structure: see text] A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield of 13%.
Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.
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