Rhodium‐Catalyzed Enantioselective and Diastereoselective Hydrogenation of β‐Ketoenamides: Efficient Access to anti 1,3‐Amino Alcohols
2009; Wiley; Volume: 121; Issue: 33 Linguagem: Inglês
10.1002/ange.200902339
ISSN1521-3757
AutoresHuiling Geng, Weicheng Zhang, Jian Chen, Guohua Hou, Le Zhou, Yaping Zou, Wenjun Wu, Xumu Zhang,
Tópico(s)Catalysis for Biomass Conversion
ResumoAngewandte ChemieVolume 121, Issue 33 p. 6168-6170 Zuschrift Rhodium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of β-Ketoenamides: Efficient Access to anti 1,3-Amino Alcohols† Huiling Geng, Huiling Geng College of Science, Northwest Agriculture & Forestry University, Yangling, Shaanxi 712100 (China) Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorWeicheng Zhang, Weicheng Zhang Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorJian Chen, Jian Chen Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorGuohua Hou, Guohua Hou Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorLe Zhou Prof., Le Zhou Prof. College of Science, Northwest Agriculture & Forestry University, Yangling, Shaanxi 712100 (China)Search for more papers by this authorYaping Zou, Yaping Zou Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorWenjun Wu Prof., Wenjun Wu Prof. [email protected] College of Science, Northwest Agriculture & Forestry University, Yangling, Shaanxi 712100 (China)Search for more papers by this authorXumu Zhang Prof., Xumu Zhang Prof. [email protected] Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this author Huiling Geng, Huiling Geng College of Science, Northwest Agriculture & Forestry University, Yangling, Shaanxi 712100 (China) Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorWeicheng Zhang, Weicheng Zhang Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorJian Chen, Jian Chen Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorGuohua Hou, Guohua Hou Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorLe Zhou Prof., Le Zhou Prof. College of Science, Northwest Agriculture & Forestry University, Yangling, Shaanxi 712100 (China)Search for more papers by this authorYaping Zou, Yaping Zou Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this authorWenjun Wu Prof., Wenjun Wu Prof. [email protected] College of Science, Northwest Agriculture & Forestry University, Yangling, Shaanxi 712100 (China)Search for more papers by this authorXumu Zhang Prof., Xumu Zhang Prof. [email protected] Department of Chemistry and Chemical Biology and Department of Pharmaceutical Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854 (USA), Fax: (+1) 732-445-6312 http://rutchem.rutgers.edu/∼xumuweb/Search for more papers by this author First published: 29 July 2009 https://doi.org/10.1002/ange.200902339Citations: 17 † This research was supported by the National Institutes of Health (GM58832), China Scholarship Council, and Northwest Agriculture & Forestry University. Mass spectrometry was carried out by the Washington University Mass Spectrometry Resource, an NIH Research Resource (Grant P41RR0954). Read the full textAboutPDF ToolsRequest permissionAdd to favorites 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 Nützliche chirale Bausteine werden mit ausgezeichneter Enantio- und Diastereoselektivität bei einer Tandemhydrierung von (Z)-β-Ketoenamiden gebildet, die wiederum durch direkte Kondensation von 1,3-Diketonen mit Acetamid erhalten werden (siehe Schema). Die chiralen Aminoalkoholprodukte können durch Hydrogenolyse mit Pd/C in nützliche γ-Arylisobutylamine überführt werden. R1=Aryl, Heteroaryl, Methyl; R2=Alkyl. 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 ange_200902339_sm_miscellaneous_information.pdf6.3 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. References 1M. Nogradi, Stereoselective Synthesis, VCH, Weinheim, 1987. Google Scholar 2S. M. Lait, D. A. Rankic, B. A. Keay, Chem. Rev. 2007, 107, 767. 10.1021/cr050065q CASPubMedWeb of Science®Google Scholar 3T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. 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