Synthesis 2020; 52(04): 553-564
DOI: 10.1055/s-0039-1690745
paper
© Georg Thieme Verlag Stuttgart · New York

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

Guillaume Force
a  Institut 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
b  Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France
,
Régis Guillot
a  Institut 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
,
a  Institut 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
b  Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France
,
a  Institut 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
› Author Affiliations
We gratefully thank the Agence Nationale de la Recherche (ANR-16-CE07-0022 funding for G.F.).
Further Information

Publication History

Received: 03 September 2019

Accepted after revision: 25 October 2019

Publication Date:
11 November 2019 (online)


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.

Supporting Information

 
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