Formal [8+3]-Annulation between Azaoxyallyl Cations and Tropones

Guillaume Force; Amélie Pérot; Régis Guillot; Vincent Gandon; David Leboeuf

doi:10.1055/s-0039-1690745

Synthesis, Table of Contents

Synthesis 2020; 52(04): 553-564
DOI: 10.1055/s-0039-1690745

paper

Formal [8+3]-Annulation between Azaoxyallyl Cations and Tropones

Guillaume Force

^aInstitut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France Email: vincent.gandon@u-psud.fr Email: david.leboeuf@u-psud.fr

,

Amélie Pérot

^bLaboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France

,

Régis Guillot

^aInstitut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France Email: vincent.gandon@u-psud.fr Email: david.leboeuf@u-psud.fr

,

Vincent Gandon ∗

^aInstitut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France Email: vincent.gandon@u-psud.fr Email: david.leboeuf@u-psud.fr

^bLaboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France

,

David Leboeuf ∗

^aInstitut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France Email: vincent.gandon@u-psud.fr Email: david.leboeuf@u-psud.fr

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Abstract

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Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry

Abstract

For the first time, azaoxyallyl cations were used as cycloaddition partners with tropone derivatives to access nitrogen-containing [7,6]-fused bicycles in a metal-free process under mild reaction conditions. DFT computations have been used to shed light on the selectivities observed during the course of the reaction.

Key words

tropone - α-haloamide - azaoxyallyl cation - cycloaddition - DFT computations

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References

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