Journal
CHEMICAL SCIENCE
Volume 8, Issue 3, Pages 1977-1980Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc03764j
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Funding
- National Natural Science Foundation of China
- National Basic Research Program of China [2012CB821600]
- 111 project of the Ministry of Education of China [B06005]
- National Program for Support of Top-notch Young Professionals
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We developed neutral iridium catalysts with chiral spiro phosphine-carboxy ligands (SpiroCAP) for asymmetric hydrogenation of unsaturated carboxylic acids. Different from the cationic Crabtree-type catalysts, the iridium catalysts with chiral spiro phosphine-carboxy ligands are neutral and do not require the use of a tetrakis[3,5-bis(trifluoromethyl) phenyl] borate (BArF-) counterion, which is necessary for stabilizing cationic Crabtree-type catalysts. Another advantage of the neutral iridium catalysts is that they have high stability and have a long lifetime in air. The new iridium catalysts with chiral spiro phosphine-carboxy ligands exhibit unprecedented high enantioselectivity (up to 99.4% ee) in the asymmetric hydrogenations of various unsaturated carboxylic acids, particularly for 3-alkyl-3-methylenepropionic acids, which are challenging substrates for other chiral catalysts.
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