Preparation of Cyclopent-2-enone Derivatives via the Aza-Piancatelli Rearrangement
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چکیده
منابع مشابه
Sequential aza-Piancatelli rearrangement/Friedel-Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives.
2-Furylcarbinols undergo a smooth aza-Piancatelli rearrangement followed by Friedel-Crafts alkylation with a bifunctional substrate, (1H-pyrrol-1-yl)aniline, in the presence of 10 mol% In(OTf)3 in acetonitrile at room temperature to afford the corresponding hexahydrobenzo[b]cyclopenta[f]pyrrolo[1,2-d][1,4]diazepin-11(4aH)-one scaffolds in good yields. This method offers significant advantages s...
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The observed rate of reaction in the dysprosium triflate catalyzed aza-Piancatelli rearrangement is controlled by a key off-cycle binding between aniline and catalyst. Deconvoluting the role of these ancillary species greatly broadens our understanding of factors affecting the productive catalytic pathway. We demonstrate that the rate of reaction is controlled by initial competitive binding bet...
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Well-represented in natural products and biologically active molecules, the cyclopentenone scaffold has long been an inspiration for the development of new methodologies. In 1976, Piancatelli and co-workers reported a new method for the synthesis of 4-hydroxycyclopentenone derivatives by an acid-catalyzed rearrangement of suitable 2-furylcarbinols (Scheme 1). The overall transformation is belie...
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number of elegant approaches to construct azaspirocycles have been developed. The methods differ in the strategy used to address the two main synthetic challenges: construction of the tertiary carbon center bearing the nitrogen atom, and the formation of the spirocyclic ring system. Generally, the synthetic routes rely on a two-step process where the tertiary carbon center and the spirocycle ar...
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The development of a new platform to initiate the cascade rearrangement of furans for the formation of functionalized cyclopentenone building blocks is reported. This methodology allows the creation of congested vicinal stereogenic centers with high diastereoselectivity through a 4π-electrocyclization process.
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ژورنال
عنوان ژورنال: Organic Syntheses
سال: 2018
ISSN: 2333-3553
DOI: 10.15227/orgsyn.095.0046