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aza piancatelli

Boubacar Baldé, Guillaume Force, Lucile Marin, Régis Guillot, Emmanuelle Schulz, Vincent Gandon, David Lebœuf
A new and efficient reaction sequence between 2-furylcarbinols, anilines, and α-haloamides has been developed to afford highly functionalized cyclopenta[ b]piperazinones. This transformation was accomplished through an aza-Piancatelli cyclization/azaoxyallyl cation trapping with a complete control of the diastereoselectivity.
November 27, 2018: Organic Letters
Zhong-Li Xu, Ping Xing, Biao Jiang
A novel method for the construction of 1-azaspirocycles from 5-alkyl-/-arylamine furylcarbinols though intramolecular aza-Piancatelli rearrangement was developed. By using PPh3 /diethyl azodicarboxylate instead of a Lewis acid, 1-azaspirocyclic compounds were obtained in good yields and the reaction temperature was reduced to room temperature. In addition, substrates with groups that are sensitive to high temperatures or Lewis acids are tolerated under these reaction conditions. This is the first method that is applicable not only to 5-(N-arylaminoalkyl)furylcarbinols with better yields but also to 5-(N-alkylaminoalkyl)furylcarbinols...
March 3, 2017: Organic Letters
Huilin Li, Rongbiao Tong, Jianwei Sun
An efficient organocatalytic enantioselective aza-Piancatelli rearrangement is disclosed. The powerful process provides rapid access to valuable chiral 4-amino-2-cyclopentenone building blocks from readily available 2-furfurylcarbinols with excellent chemo-, enantio-, and diastereoselectivities under mild reaction conditions.
November 21, 2016: Angewandte Chemie
Yunfei Cai, Yurong Tang, Iuliana Atodiresei, Magnus Rueping
The first catalytic asymmetric Piancatelli reaction is reported. Catalyzed by a chiral Brønsted acid, the rearrangement of a wide range of furylcarbinols with a series of aniline derivatives provides valuable aminocyclopentenones in high yields as well as excellent enantioselectivities and diastereoselectivities. The high value of the aza-Piancatelli rearrangement was demonstrated by the synthesis of a cyclopentane-based hNK1 antagonist analogue.
November 2, 2016: Angewandte Chemie
David Lebœuf, Lucile Marin, Bastien Michelet, Alejandro Perez-Luna, Régis Guillot, Emmanuelle Schulz, Vincent Gandon
A method to extend the scope of the aza-Piancatelli reaction between 2-furylcarbinols and anilines is depicted. We found that 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) is the solvent of choice for this transformation, as it outcompetes the usual solvents in terms of rate and yield. Side reactions and other issues raised by the title reaction are prevented, thereby providing an avenue to complex molecules that were previously inaccessible. Lewis acidity studies and computations were carried out to unveil the role of HFIP...
November 2, 2016: Chemistry: a European Journal
B V Subba Reddy, Y Vikram Reddy, Kiran Kumar Singarapu
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 such as high conversions, mild reaction conditions, short reaction times, and high selectivity. The relative stereochemistry of the product was established by nOe studies...
January 21, 2016: Organic & Biomolecular Chemistry
Gesine K Veits, Donald R Wenz, Leoni I Palmer, André H St Amant, Jason E Hein, Javier Read de Alaniz
This article describes the aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones and subsequent transformations that highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine nucleophile in this transformation.
August 21, 2015: Organic & Biomolecular Chemistry
David Lebœuf, Emmanuelle Schulz, Vincent Gandon
The first examples of calcium-catalyzed aza-Piancatelli reactions between substituted 2-furylcarbinols and aniline derivatives are described. A variety of 4-aminocyclopentenones have been synthesized stereoselectively in high yields. The experimental procedure utilizes simple salts and does not require specific precautions.
December 19, 2014: Organic Letters
Diana Yu, Van T Thai, Leoni I Palmer, Gesine K Veits, Jonathan E Cook, Javier Read de Alaniz, Jason E Hein
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 between the furylcarbinol and nitrogen nucleophile using either a Brønsted or Lewis acid catalyst and that the resulting rearrangement proceeds without involving the Brønsted and Lewis acid catalyst...
December 20, 2013: Journal of Organic Chemistry
Donald R Wenz, Javier Read de Alaniz
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.
July 5, 2013: Organic Letters
Leoni I Palmer, Javier Read de Alaniz
No abstract text is available yet for this article.
July 25, 2011: Angewandte Chemie
Gesine K Veits, Donald R Wenz, Javier Read de Alaniz
No abstract text is available yet for this article.
December 3, 2010: Angewandte Chemie
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