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Issue 15, 2019
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BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions

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Abstract

In this work we have found that a BODIPY can be used as an electron withdrawing group for the activation of double bonds in asymmetric catalysis. The synthesis of cyclohexyl derivatives containing a BODIPY unit can easily be achieved via trienamine catalysis. This allows a new different asymmetric synthesis of BODIPY derivatives and opens the door to future transformation of this useful fluorophore. In addition, the Quantum Chemistry calculations and mechanistic studies provide insights into the role of BODIPY as an EWG.

Graphical abstract: BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions

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Supplementary files

Article information


Submitted
25 Feb 2019
Accepted
13 Mar 2019
First published
20 Mar 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 4346-4351
Article type
Edge Article

BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions

A. Guerrero-Corella, J. Asenjo-Pascual, T. J. Pawar, S. Díaz-Tendero, A. Martín-Sómer, C. V. Gómez, J. L. Belmonte-Vázquez, D. E. Ramírez-Ornelas, E. Peña-Cabrera, A. Fraile, D. C. Cruz and J. Alemán, Chem. Sci., 2019, 10, 4346
DOI: 10.1039/C9SC00959K

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