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Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides

The MaxPHOX–Ir catalyst system provided the highest selectivity ever reported for the reduction of cyclic enamides derived from α‐ and β‐tetralones. This result indicates that iridium catalysts are also proficient in reducing alkenes bearing metal‐coordinating groups. In the present system, selectiv...

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Autores principales: Salomó, Ernest, Orgué, Sílvia, Riera, Antoni, Verdaguer, Xavier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5084810/
https://www.ncbi.nlm.nih.gov/pubmed/27186653
http://dx.doi.org/10.1002/anie.201602219
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author Salomó, Ernest
Orgué, Sílvia
Riera, Antoni
Verdaguer, Xavier
author_facet Salomó, Ernest
Orgué, Sílvia
Riera, Antoni
Verdaguer, Xavier
author_sort Salomó, Ernest
collection PubMed
description The MaxPHOX–Ir catalyst system provided the highest selectivity ever reported for the reduction of cyclic enamides derived from α‐ and β‐tetralones. This result indicates that iridium catalysts are also proficient in reducing alkenes bearing metal‐coordinating groups. In the present system, selectivity was pressure‐dependent: In most cases, a decrease in the H(2) pressure to 3 bar resulted in an increase in enantioselectivity. Moreover, the process can be carried out in environmentally friendly solvents, such as methanol and ethyl acetate, with no loss of selectivity.
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spelling pubmed-50848102016-11-09 Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides Salomó, Ernest Orgué, Sílvia Riera, Antoni Verdaguer, Xavier Angew Chem Int Ed Engl Communications The MaxPHOX–Ir catalyst system provided the highest selectivity ever reported for the reduction of cyclic enamides derived from α‐ and β‐tetralones. This result indicates that iridium catalysts are also proficient in reducing alkenes bearing metal‐coordinating groups. In the present system, selectivity was pressure‐dependent: In most cases, a decrease in the H(2) pressure to 3 bar resulted in an increase in enantioselectivity. Moreover, the process can be carried out in environmentally friendly solvents, such as methanol and ethyl acetate, with no loss of selectivity. John Wiley and Sons Inc. 2016-05-17 2016-07-04 /pmc/articles/PMC5084810/ /pubmed/27186653 http://dx.doi.org/10.1002/anie.201602219 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) 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
Salomó, Ernest
Orgué, Sílvia
Riera, Antoni
Verdaguer, Xavier
Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides
title Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides
title_full Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides
title_fullStr Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides
title_full_unstemmed Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides
title_short Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides
title_sort highly enantioselective iridium‐catalyzed hydrogenation of cyclic enamides
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5084810/
https://www.ncbi.nlm.nih.gov/pubmed/27186653
http://dx.doi.org/10.1002/anie.201602219
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