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

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.

SUBMITTER: Guerrero-Corella A

PROVIDER: S-EPMC6472058 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Guerrero-Corella Andrea A Asenjo-Pascual Juan J Pawar Tushar Janardan TJ Díaz-Tendero Sergio S Martín-Sómer Ana A Gómez Clarisa Villegas CV Belmonte-Vázquez José L JL Ramírez-Ornelas Diana E DE Peña-Cabrera Eduardo E Fraile Alberto A Cruz David Cruz DC Alemán José J Alemán José J

Chemical science 20190320 15

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 <i>via</i> 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 i ...[more]

PMID: 31057762

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