Bi(OTf) 3 -Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis- N -Acyliminium Species in a Tandem Process

Ahmed Aliyenne; Frédéric Pin; Vijaykumar Nimbarte; Ata Martin Lawson; Sébastien Comesse; Morgane Sanselme; Vincent Tognetti; Laurent Joubert; Adam Daïch

doi:10.1002/ejoc.201600530

Journal articles

Bi(OTf) 3 -Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis- N -Acyliminium Species in a Tandem Process

Ahmed Aliyenne ¹ Frédéric Pin ¹ Vijaykumar Nimbarte ¹ Ata Martin Lawson ¹ Sébastien Comesse ¹ Morgane Sanselme ² Vincent Tognetti ³ Laurent Joubert ³ Adam Daïch ¹

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire

2 SMS - Sciences et Méthodes Séparatives

3 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Abstract : Isoindolinones and tricyclic N,O‐acetals are obtained from bis‐N‐acyliminium precursors and assorted nucleophiles using catalytic Bi(OTf)3. The reactions proceed, respectively, through a double amidoalkylation or tandem π‐cyclisation/α‐oxa‐amidoalkylation. Mechanistic aspects of the tandem chemistry are supported by DFT calculations and its utility in RCM and Click reactions illustrated. New 1,3‐bis‐N‐acyliminium species generated easily with nontoxic Bi(OTf)3 catalyst at very low loadings (2 mol‐%) were trapped inter‐ and intramolecularly with various poly‐nucleophiles. This mild, efficient, practical and general tandem approach provides an array of substituted isoindolinones and cyclic N,O‐acetals.

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Journal articles

Domain :

Chemical Sciences

Chemical Sciences / Cristallography

Chemical Sciences / Inorganic chemistry

Chemical Sciences / Organic chemistry

Chemical Sciences / Material chemistry

Chemical Sciences / Theoretical and/or physical chemistry

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https://hal-normandie-univ.archives-ouvertes.fr/hal-01928678
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Submitted on : Tuesday, November 20, 2018 - 4:41:26 PM
Last modification on : Thursday, July 2, 2020 - 3:28:44 AM

Bi(OTf) 3 -Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis- N -Acyliminium Species in a Tandem Process

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Bi(OTf) 3 -Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis- N -Acyliminium Species in a Tandem Process

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