Asymmetric Hydrogenation of 2,4‐Disubstituted 1,5‐Benzodiazepines Using Cationic Ruthenium Diamine Catalysts: An Unusual Achiral Counteranion Induced Reversal of Enantioselectivity

Angewandte Chemie International EditionVolume 51, Issue 23 p. 5706-5710 Communication Asymmetric Hydrogenation of 2,4-Disubstituted 1,5-Benzodiazepines Using Cationic Ruthenium Diamine Catalysts: An Unusual Achiral Counteranion Induced Reversal of Enantioselectivity† Zi-Yuan Ding, Zi-Yuan Ding Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorFei Chen, Fei Chen Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorJie Qin, Jie Qin Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorYan-Mei He, Yan-Mei He Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorProf. Dr. Qing-Hua Fan, Corresponding Author Prof. Dr. Qing-Hua Fan [email protected] Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this author Zi-Yuan Ding, Zi-Yuan Ding Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorFei Chen, Fei Chen Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorJie Qin, Jie Qin Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorYan-Mei He, Yan-Mei He Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this authorProf. Dr. Qing-Hua Fan, Corresponding Author Prof. Dr. Qing-Hua Fan [email protected] Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190 (P. R. China)Search for more papers by this author First published: 24 April 2012 https://doi.org/10.1002/anie.201200309Citations: 101 † Financial support from the National Basic Research Program of China (973 Program, Nos. 2010CB833300 and 2011CB808600), the National Natural Science Foundation of China (Grant No 20973178), and the Chinese Academy of Sciences is greatly 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 BArFing it out the other way: A highly enantioselective hydrogenation of 2,4-disubstituted 1,5-benzodiazepines using chiral cationic ruthenium diamine catalysts (R,R)-1 has been developed (see scheme; BArF=tetrakis(3,5-bistrifluoromethylphenyl)borate). Either enantiomer of 2,4-diaryl-2,3,4,5-tetrahydro-1H-benzodiazepine derivatives could be obtained by using the same enantiomer of ligand but in the presence of a different achiral counteranion. 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_201200309_sm_miscellaneous_information.pdf6.9 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. Volume51, Issue23June 4, 2012Pages 5706-5710 RelatedInformation