![Accessing Dihydropyrrolo[3,4‐b]indol‐1(2H)‐ones via Pd‐Catalyzed Intramolecular Aminocarbonylative Ring Closure](https://chemistry-europe.onlinelibrary.wiley.com/cms/asset/1eed5148-9b12-4168-beae-d3aff57cd88f/ejoc202300646-toc-0001-m.png)
The dihydropyrrolo[3,4-b]indol-1(2H)-one (DHPI) scaffold is present in a range of biologically active small molecules. Focusing on the development of a transition metal-catalyzed intramolecular aminocarbonylation of the 1H-in...
Artikel
Regioselective Synthesis of 2‐Trimethylsilyl‐4H‐pyran‐4‐ones from 1‐Ethoxy(hydroxy)‐5‐(trimethylsilyl)pentenynones
Von Wiley-VCH zur Verfügung gestellt
Pyran-4-ones with unique substitution pattern can be accessed via regioselective 6-endo-dig cyclization of 1-[O]-enynones; mechanistic explanations were proposed. Thiation and desilylation of TMS-substituted pyranones can be easily performed.
Abstract
Exclusive formation of 5-aryl-2-trimethylsilyl-4H-pyran-4-ones is accomplished by a regioselective cyclization of 2-aryl-1-ethoxy(hydroxy)-5-(trimethylsilyl)pent-1-en-4-yn-3-ones. This cyclization occurs in a 6-endo-dig mode through addition to the β-atom of the TMS substituted triple bond. The reaction was found to be general for a range of ethoxyenynones upon heating in glacial acetic acid and for analogous hydroxyenynones in diphenyl ether. Plausible mechanistic explanation and possible post-modifications of resulting pyranones are offered.
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