886-38-4Relevant articles and documents
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Breslow,R. et al.
, p. 234 (1963)
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Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines
Heiss, Tyler K.,Prescher, Jennifer A.
, p. 7443 - 7448 (2019)
We report a new ligation of cyclopropeniminium ions with bioorthogonal phosphines. Cyclopropeniminium scaffolds are sufficiently stable in biological media and, unlike related isomers, react with functionalized phosphines via formal 1,2-addition to a I-system. The ligation can be performed in aqueous solution and is compatible with existing bioorthogonal transformations. Such mutually compatible reactions are useful for multicomponent labeling.
Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides
Nanda, Tanmayee,Biswal, Pragati,Pati, Bedadyuti Vedvyas,Banjare, Shyam Kumar,Ravikumar, Ponneri Chandrababu
, p. 2682 - 2695 (2021/02/01)
Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in the product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive molecules such as procaine, estrone, and hymecromone demonstrates the robustness of this protocol.
Rh(III)-Catalyzed [3 + 3] Annulation Reaction of Cyclopropenones and Sulfoxonium Ylides toward Trisubstituted 2-Pyrones
Zhou, Peng,Yang, Wei-Tao,Rahman, Anis Ur,Li, Guigen,Jiang, Bo
, p. 360 - 366 (2019/11/14)
A new Rh(III)-catalyzed [3 + 3] annulation reaction between cyclopropenones and β-ketosulfoxonium ylides has been reported, enabling metal carbene insertion to access a wide range of trisubstituted 2-pyrones with moderate to excellent yields via C-C single-bond cleavage, in which sulfoxonium ylides serve as potential safe precursors of metal carbenes. This reaction occurred under redox-neutral conditions with a broad substrate scope.