2020
DOI: 10.1021/acs.chemrev.0c00166
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Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives

Abstract: This review summarizes synthetic developments reported from 1987 to 2019 that exploit C–C single bond cleavage of cyclopropylamine-based systems. The synthetic and mechanistic aspects of key methodologies are highlighted, and examples where aminocyclopropanes are exploited as key intermediates in multistep synthesis are also discussed. The review encompasses cases where aminocyclopropanes participate in polar reactions, pericyclic processes, radical-based reactions, and C–C bond activations.

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Cited by 110 publications
(72 citation statements)
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“…As mentioned in the introductory section of this review, the release of the strain of carbocyclic structures is one of the driving forces that can promote the cleavage of C–C bonds [ 26 ], generating intermediates of different nature depending on the experimental conditions which can further evolve intra- or intermolecularly to afford new organic scaffolds. This section presents recent progress carried out on the different approaches where the functionalization of a C–H bond is achieved through the use of cyclopropyl and cyclobutyl scaffolds [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ].…”
Section: Synthetic Methodology Involving C–h Functionalization Alomentioning
confidence: 99%
“…As mentioned in the introductory section of this review, the release of the strain of carbocyclic structures is one of the driving forces that can promote the cleavage of C–C bonds [ 26 ], generating intermediates of different nature depending on the experimental conditions which can further evolve intra- or intermolecularly to afford new organic scaffolds. This section presents recent progress carried out on the different approaches where the functionalization of a C–H bond is achieved through the use of cyclopropyl and cyclobutyl scaffolds [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ].…”
Section: Synthetic Methodology Involving C–h Functionalization Alomentioning
confidence: 99%
“…[42][43][44][45] It is a general building block as well to prepare valuable architectures via ringopening reactions. [46][47][48][49] Herein, we describe the Rh 2 (esp) 2 catalyzed cyclopropanation of N-tosyl substituted enamides with cyclopropenes to construct vicinal trisubstituted cyclopropyl cores with good E/Z and syn/anti stereoselectivities. The small rings were further exploited to undergo regioselectively oxidative ring-opening reactions to deliver conjugated 1,3-dienyl aldehydes under silver and copper co-catalytic systems.…”
Section: Introductionmentioning
confidence: 99%
“…Such carboacylation reactions have been extensively demonstrated in strained ring systems. [21][22][23][24][25][26] However, there are only a few known examples of unstrained systems, such as those reported by Douglas and Dong, and the regioselectivity of this reaction remains largely unexplored. [27][28][29][30] Motivated by the importance of directly forming indane rings, we envisioned using ketones as aldehyde surrogates in catalytic C-C activation.…”
Section: Introductionmentioning
confidence: 99%