Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202301628
Keywords
Asymmetric Synthesis; Chiral Phosphorus Compounds; Copper Catalysis; P-Stereogenic Compounds; Transition Metal Catalysis
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We report a highly enantioselective dynamic kinetic intermolecular P-C coupling of secondary phosphine oxides (SPOs) and aryl iodides catalyzed by copper complexes ligated by a finely modified chiral 1,2-diamine ligand. The reaction tolerates a wide range of substrates, providing P-stereogenic phosphine oxides in high yields and with good enantioselectivity. The resulting enantioenriched products can be transformed into structurally diverse P-chiral scaffolds, which are valuable in asymmetric synthesis as ligands and catalysts.
Transition-metal-catalyzed enantioselective P-C cross-coupling of secondary phosphine oxides (SPOs) is an attractive method for synthesizing P-stereogenic phosphorus compounds, but the development of such a dynamic kinetic asymmetric process remains a considerable challenge. Here we report an unprecedented highly enantioselective dynamic kinetic intermolecular P-C coupling of SPOs and aryl iodides catalyzed by copper complexes ligated by a finely modified chiral 1,2-diamine ligand. The reaction tolerates a wide range of SPOs and aryl iodides, affording P-stereogenic tertiary phosphine oxides (TPOs) in high yields and with good enantioselectivity (average 89.2 % ee). The resulting enantioenriched TPOs were transformed into structurally diverse P-chiral scaffolds, which are highly valuable as ligands and catalysts in asymmetric synthesis.
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