Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis

A stereoselective one-pot synthesis of spiropyrazolones through an organocatalytic asymmetric Michael addition and a formal Conia-ene reaction has been developed. Depending on the nitroalkene, the 5-exo-dig-cyclization could be achieved by silver-catalyzed alkyne activation or by oxidation of the in...

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Autores principales: Hack, Daniel, Dürr, Alexander B, Deckers, Kristina, Chauhan, Pankaj, Seling, Nico, Rübenach, Lukas, Mertens, Lucas, Raabe, Gerhard, Schoenebeck, Franziska, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley & Sons, Ltd 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4725220/
https://www.ncbi.nlm.nih.gov/pubmed/26676875
http://dx.doi.org/10.1002/anie.201510602
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author Hack, Daniel
Dürr, Alexander B
Deckers, Kristina
Chauhan, Pankaj
Seling, Nico
Rübenach, Lukas
Mertens, Lucas
Raabe, Gerhard
Schoenebeck, Franziska
Enders, Dieter
author_facet Hack, Daniel
Dürr, Alexander B
Deckers, Kristina
Chauhan, Pankaj
Seling, Nico
Rübenach, Lukas
Mertens, Lucas
Raabe, Gerhard
Schoenebeck, Franziska
Enders, Dieter
author_sort Hack, Daniel
collection PubMed
description A stereoselective one-pot synthesis of spiropyrazolones through an organocatalytic asymmetric Michael addition and a formal Conia-ene reaction has been developed. Depending on the nitroalkene, the 5-exo-dig-cyclization could be achieved by silver-catalyzed alkyne activation or by oxidation of the intermediate enolate. The mechanistic pathways have been investigated using computational chemistry and mechanistic experiments.
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spelling pubmed-47252202016-02-03 Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis Hack, Daniel Dürr, Alexander B Deckers, Kristina Chauhan, Pankaj Seling, Nico Rübenach, Lukas Mertens, Lucas Raabe, Gerhard Schoenebeck, Franziska Enders, Dieter Angew Chem Int Ed Engl Communications A stereoselective one-pot synthesis of spiropyrazolones through an organocatalytic asymmetric Michael addition and a formal Conia-ene reaction has been developed. Depending on the nitroalkene, the 5-exo-dig-cyclization could be achieved by silver-catalyzed alkyne activation or by oxidation of the intermediate enolate. The mechanistic pathways have been investigated using computational chemistry and mechanistic experiments. John Wiley & Sons, Ltd 2016-01-26 2015-12-16 /pmc/articles/PMC4725220/ /pubmed/26676875 http://dx.doi.org/10.1002/anie.201510602 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by-nc/4.0/ This is an open access article under the terms of the Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Hack, Daniel
Dürr, Alexander B
Deckers, Kristina
Chauhan, Pankaj
Seling, Nico
Rübenach, Lukas
Mertens, Lucas
Raabe, Gerhard
Schoenebeck, Franziska
Enders, Dieter
Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis
title Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis
title_full Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis
title_fullStr Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis
title_full_unstemmed Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis
title_short Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis
title_sort asymmetric synthesis of spiropyrazolones by sequential organo- and silver catalysis
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4725220/
https://www.ncbi.nlm.nih.gov/pubmed/26676875
http://dx.doi.org/10.1002/anie.201510602
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