Journal
ORGANIC LETTERS
Volume 18, Issue 9, Pages 2122-2125Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00748
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Funding
- National Natural Science Foundation of China [21372152, 21402117, 21232004]
- Science and Technology Commission of Shanghai Municipality [14XD1402300]
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Asymmetric hydrogenation of various alpha-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H-2, affording the corresponding chiral alpha-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.
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