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Rhodium(II)/Chiral Phosphoric Acid‐Cocatalyzed Enantioselective O–H Bond Insertion of α‐Diazo Esters
Author(s) -
Zhang Yiliang,
Yao Yuan,
He Li,
Liu Yang,
Shi Lei
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700572
Subject(s) - chemistry , diazo , rhodium , phosphoric acid , enantioselective synthesis , yield (engineering) , insertion reaction , substrate (aquarium) , catalysis , organic chemistry , phenols , combinatorial chemistry , medicinal chemistry , materials science , oceanography , metallurgy , geology
A rhodium(II)/chiral phosphoric acid system has been developed for the asymmetric catalytic insertion of α‐diazo esters into the O–H bond of carboxylic acids to generate an array of synthetically useful α‐hydroxy ester derivatives in good ee (up to 95% ee ). Furthermore, the substrate scope could be successfully extended to a range of phenols and alcohols with high yield (up to 92%) and excellent enantioselectivity (up to 97%) under mild reaction conditions. Additionally, a density functional theory (DFT) study was performed to elucidate the reaction mechanism.