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Highly Enantioselective Hydroxycarbonylation and Alkoxycarbonylation of Alkenes using Dipalladium Complexes as Precatalysts

2010; Wiley; Volume: 49; Issue: 48 Linguagem: Inglês

10.1002/anie.201004415

ISSN

1521-3773

Autores

Tina Maria Konrad, José A. Fuentes, Alexandra M. Z. Slawin, Matthew L. Clarke,

Tópico(s)

Organometallic Complex Synthesis and Catalysis

Resumo

Angewandte Chemie International EditionVolume 49, Issue 48 p. 9197-9200 Communication Highly Enantioselective Hydroxycarbonylation and Alkoxycarbonylation of Alkenes using Dipalladium Complexes as Precatalysts† Tina M. Konrad, Tina M. Konrad School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this authorDr. José A. Fuentes, Dr. José A. Fuentes School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this authorProf. Alexandra M. Z. Slawin, Prof. Alexandra M. Z. Slawin School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this authorDr. Matthew L. Clarke, Corresponding Author Dr. Matthew L. Clarke [email protected] School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this author Tina M. Konrad, Tina M. Konrad School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this authorDr. José A. Fuentes, Dr. José A. Fuentes School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this authorProf. Alexandra M. Z. Slawin, Prof. Alexandra M. Z. Slawin School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this authorDr. Matthew L. Clarke, Corresponding Author Dr. Matthew L. Clarke [email protected] School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, Scotland (UK), Fax: (+44) 1334-463808Search for more papers by this author First published: 26 October 2010 https://doi.org/10.1002/anie.201004415Citations: 92 † We thank the University of St Andrews and the European Union ITN, Nanohost for financial support (T.M.K.), and Dr. Reddys CPS-Chirotech for a grant to develop this technology. We thank Dr. Chris Cobley (Dr. Reddys CPS-Chirotech) for fruitful discussions. Technical support at the University of St Andrews is also gratefully acknowledged. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract Joined at Pd: Novel palladium catalysts like 1, in which the planar-chiral phosphine acts as a bridging ligand, have been developed. These dimetallic complexes are highly enantioselective catalysts in the hydroxycarbonylation of alkenes, a reaction that has proven problematic over the years. PTSA=para-toluenesulfonic acid. References 1 1aW. Clegg, G. R. Eastham, M. R. J. Elsegood, R. P. Tooze, X. L. Wang, K. Whiston, Chem. Commun. 1999, 1877; 1bC. Jimenez Rodriguez, D. F. Foster, G. R. Eastham, D. J. 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A 2000, 161, 39; 4bA preliminary report of an enantioselective carbonylation using binaphthyl phosphoric acid ligands appeared some time ago, but unfortunately yields were moderate and over 10 % catalyst was required along with three promoters (CuCl2, HCl, and oxygen). H. Alper, N. Hamel, J. Am. Chem. Soc. 1990, 112, 2803; 4cOnly 8–38 % ee was realized in alkoxycarbonylations using the same system: Y. Kewu, J. Zuanzhen, Chem. J. Internet 2005, 7, 14; 4dM. Dolors Miquel-Serrano, A. Aghmiz, M. Diéguez, A. M. Masdeu-Bultó, C. Claver, D. Sinou, Tetrahedron: Asymmetry 1999, 10, 4463. 5The nearest precedents we have found for dimeric metal halides of chiral bridging diphosphines are quite far removed: 5aAchiral dimeric hydroformylation catalysts: D. A. Aubry, N. N. Bridges, K. Ezell, G. G. Stanley, J. Am. Chem. Soc. 2003, 125, 11180; 5bChiral dipalladium complexes of a special bridging triketonate ligand in asymmetric oxidation: A. K. El-Qisairi, H. A. Qaseer, P. M. Henry, J. Organomet. 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Soc. 1991, 113, 113. 10J. F. Knifton, J. Org. Chem. 1976, 41, 2885. 11T. M. Konrad and M. L. Clarke (University of St Andrews), PCT Application 0915946.8, 2009. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201004415_sm_miscellaneous_information.pdf1.3 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume49, Issue48November 22, 2010Pages 9197-9200 ReferencesRelatedInformation

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