A Three‐Component Reaction Based on a Remote‐Group‐Directed Dynamic Kinetic Aza‐Michael Addition: Stereoselective Synthesis of Imidazolidin‐4‐ones
2010; Wiley; Volume: 16; Issue: 10 Linguagem: Inglês
10.1002/chem.200903508
ISSN1521-3765
AutoresZhenghu Xu, Tyler Buechler, Kraig A. Wheeler, Hong Wang,
Tópico(s)Synthesis and Catalytic Reactions
ResumoChemistry – A European JournalVolume 16, Issue 10 p. 2972-2976 Communication A Three-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones Zhenghu Xu Dr., Zhenghu Xu Dr. Department of Chemistry and Biochemistry, Miami University, 701 East High Street, Oxford, OH 45056 (USA), Fax: (+1) 513 529-5715Search for more papers by this authorTyler Buechler, Tyler Buechler Department of Chemistry and Biochemistry, Miami University, 701 East High Street, Oxford, OH 45056 (USA), Fax: (+1) 513 529-5715Search for more papers by this authorKraig Wheeler Prof., Kraig Wheeler Prof. Department of Chemistry, Eastern Illinois University, 600 Lincoln Ave., Charleston, IL 61920 (USA)Search for more papers by this authorHong Wang Prof., Hong Wang Prof. [email protected] Department of Chemistry and Biochemistry, Miami University, 701 East High Street, Oxford, OH 45056 (USA), Fax: (+1) 513 529-5715Search for more papers by this author Zhenghu Xu Dr., Zhenghu Xu Dr. Department of Chemistry and Biochemistry, Miami University, 701 East High Street, Oxford, OH 45056 (USA), Fax: (+1) 513 529-5715Search for more papers by this authorTyler Buechler, Tyler Buechler Department of Chemistry and Biochemistry, Miami University, 701 East High Street, Oxford, OH 45056 (USA), Fax: (+1) 513 529-5715Search for more papers by this authorKraig Wheeler Prof., Kraig Wheeler Prof. Department of Chemistry, Eastern Illinois University, 600 Lincoln Ave., Charleston, IL 61920 (USA)Search for more papers by this authorHong Wang Prof., Hong Wang Prof. [email protected] Department of Chemistry and Biochemistry, Miami University, 701 East High Street, Oxford, OH 45056 (USA), Fax: (+1) 513 529-5715Search for more papers by this author First published: 01 March 2010 https://doi.org/10.1002/chem.200903508Citations: 17Read 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 In control: An α-amino amide reacted with an aldehyde and a Michael acceptor to form stable imidazolidin-4-ones with high stereoselectivity. A dynamic kinetic aza-Michael addition was discovered and applied to the three-component reaction to enforce high stereoselectivity. A remote group was incorporated to invert the reaction process and direct the reaction towards the desired product (see scheme). 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 chem_200903508_sm_miscellaneous_information.pdf7.9 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. 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