期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 40, 页码 13883-13887出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502718
关键词
asymmetric catalysis; dearomatization; oxabicycles; rhodium; ring opening reactions
资金
- National Sciences and Engineering Research Council (NSERC)
- University of Toronto
- Alphora Inc.
- Deutsche Forschungsgemeinschaft (DFG) [LO 2065/1-1]
- National Natural Science Foundation of China [21172148, 21202044]
- China Scholarship Council [201306745008]
- NSERC
While anthrones exist as privileged scaffolds in bioactive molecules, the enantioselective functionalization of anthrones is surprisingly scarce in the literature, with no asymmetric transition metal catalyzed example to date. Herein, we report the first asymmetric transition metal catalyzed benzylic functionalization of anthrones through the rhodium(I) catalyzed desymmetrization of oxabicycles. As previously developed rhodium(I) systems were found to be unsuitable for this substrate, a new robust fourth-generation [Rh(cod)OH](2) based catalytic system was developed to address synthetic challenges in this protocol.
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