Enantioselective Synthesis of P‐Stereogenic Phosphinates and Phosphine Oxides by Molybdenum‐Catalyzed Asymmetric Ring‐Closing Metathesis

Angewandte Chemie International EditionVolume 48, Issue 4 p. 762-766 Communication Enantioselective Synthesis of P-Stereogenic Phosphinates and Phosphine Oxides by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis† James Stephen Harvey, James Stephen Harvey Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this authorSteven J. Malcolmson, Steven J. Malcolmson Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442Search for more papers by this authorKatherine S. Dunne Dr., Katherine S. Dunne Dr. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this authorSimon J. Meek Dr., Simon J. Meek Dr. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442Search for more papers by this authorAmber L. Thompson Dr., Amber L. Thompson Dr. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this authorRichard R. Schrock Prof., Richard R. Schrock Prof. Department of Chemistry, Massachusetts Institute of Technology (USA)Search for more papers by this authorAmir H. Hoveyda Prof., Amir H. Hoveyda Prof. [email protected] Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442Search for more papers by this authorVéronique Gouverneur Prof., Véronique Gouverneur Prof. [email protected] Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this author James Stephen Harvey, James Stephen Harvey Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this authorSteven J. Malcolmson, Steven J. Malcolmson Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442Search for more papers by this authorKatherine S. Dunne Dr., Katherine S. Dunne Dr. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this authorSimon J. Meek Dr., Simon J. Meek Dr. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442Search for more papers by this authorAmber L. Thompson Dr., Amber L. Thompson Dr. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this authorRichard R. Schrock Prof., Richard R. Schrock Prof. Department of Chemistry, Massachusetts Institute of Technology (USA)Search for more papers by this authorAmir H. Hoveyda Prof., Amir H. Hoveyda Prof. [email protected] Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442Search for more papers by this authorVéronique Gouverneur Prof., Véronique Gouverneur Prof. [email protected] Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-644Search for more papers by this author First published: 05 January 2009 https://doi.org/10.1002/anie.200805066Citations: 112 † This research was financially supported by the EPSRC (DTA Award to J.S.H.), the John Fell Fund (062/214), and by the United States National Institutes of Health (GM-59426). 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The first catalytic route toward the title compounds by asymmetric ring-closing metathesis is described. A remarkable reversal of enantioselectivity is observed when the achiral imido ligand of the chiral molybdenum-catalyst is changed (see scheme), thus highlighting the importance of the achiral and the chiral ligands in catalyst design. 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_200805066_sm_miscellaneous_information.pdf428.6 KB 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. References 1 1aX. Zhang, Tetrahedron: Asymmetry 2004, 15, 2099–2100; 1bK. V. L. Crepy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1–40; 1cH. B. Kagan, P.-D Dang, J. Am. Chem. Soc. 1972, 94, 6429–6433; 1dH. B. Kagan, Asymmetric Synthesis 1985, Vol. 5, pp. 1–39; 1eJ. K. Whitesell, Chem. Rev. 1989, 89, 1581–1590. 2 2aJ. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035–1050; 2bE. Vedejs, O. Daugulis, S. T. 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Citing Literature Volume48, Issue4January 12, 2009Pages 762-766 ReferencesRelatedInformation