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Efficient Asymmetric Synthesis of a Bicyclic Amino Acid as a Core Structure of Telaprevir

2012; Wiley; Volume: 4; Issue: 7 Linguagem: Inglês

10.1002/cctc.201200081

1867-3899

Seiji Shirakawa, Yan Liu, Asuka Usui, Keiji Maruoka,

Fluorine in Organic Chemistry

ChemCatChemVolume 4, Issue 7 p. 980-982 Communication Efficient Asymmetric Synthesis of a Bicyclic Amino Acid as a Core Structure of Telaprevir Dr. Seiji Shirakawa, Dr. Seiji Shirakawa Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorDr. Yan Liu, Dr. Yan Liu Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorAsuka Usui, Asuka Usui Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorProf. Dr. Keiji Maruoka, Corresponding Author Prof. Dr. Keiji Maruoka maruoka@kuchem.kyoto-u.ac.jp Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this author Dr. Seiji Shirakawa, Dr. Seiji Shirakawa Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorDr. Yan Liu, Dr. Yan Liu Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorAsuka Usui, Asuka Usui Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this authorProf. Dr. Keiji Maruoka, Corresponding Author Prof. Dr. Keiji Maruoka maruoka@kuchem.kyoto-u.ac.jp Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041Search for more papers by this author First published: 04 April 2012 https://doi.org/10.1002/cctc.201200081Citations: 20Read 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 onFacebookTwitterLinked InRedditWechat Abstract Telaprevir building block: Efficient asymmetric synthesis of bicyclic amino acid as a core structure of telaprevir has been accomplished via phase-transfer catalyzed stereoselective conjugate addition of glycine derivative to cyclopent-1-enecarbaldehyde. This synthetic method can be applied to the asymmetric synthesis of 3-substituted prolines. 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 cctc_201200081_sm_miscellaneous_information.pdf337.4 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. Volume4, Issue7Special Issue: OrganocatalysisJuly 2012Pages 980-982 RelatedInformation