Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 39, Issue 4, Pages 933-936Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000617
Keywords
Asymmetric catalysis; Hydrogenation; Cyclic enone; Rhodium; Citral reduction
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Funding
- Science, Technology and Innovation Commission of Shenzhen [KQTD20150717103157174, JCYJ20170817104350391]
- National Natural Science Foundation of China [21801118]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
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In this study, an efficient method for reducing endocyclic enones with high enantioselectivity using molecular hydrogen catalyzed by a rhodium/Zhaophos complex is reported. This method demonstrated excellent chemo- and enantioselectivity and was successfully applied in the enantioselective hydrogenation of citral to produce enantiomer-enriched citronellal.
Main observation and conclusion The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%-99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.
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