Cu(ii)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol reaction and Domino Knoevenagel Michael cyclization : a new highly efficient Lewis acid catalyst
Al-Majid, A. M., Alammari, A. S., Alshahrani, S., Haukka, M., Islam, M. S., & Barakat, A. (2022). Cu(ii)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol reaction and Domino Knoevenagel Michael cyclization : a new highly efficient Lewis acid catalyst. RSC Advances, 12(10), 6149-6165. https://doi.org/10.1039/d2ra00674j
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RSC AdvancesAuthors
Date
2022Discipline
Epäorgaaninen ja analyyttinen kemiaEpäorgaaninen kemiaInorganic and Analytical ChemistryInorganic ChemistryCopyright
© 2022 the Authors
The highly efficient Lewis acid-catalytic system Cu(II)-thiophene-2,5-bis(amino-alcohol) has been developed for enantioselective Aldol reaction of isatin derivatives with ketones. The new catalytic system also proved to be highly enantioselective for the one pot three-component Domino Knoevenagel Michael cyclization reaction of substituted isatin with malononitrile and ethylacetoacetate. The chiral ligand (2S,2′S)-2,2′-((thiophene-2,5-diylbis(methylene))bis(azanediyl))bis(3-phenylpropan-1-ol) (L1) in combination with Cu(OAc)2·H2O employed as a new Lewis acid catalyst, furnished 3-substituted-3-hydroxyindolin-2-ones derivatives (3a–s) in good to excellent yields (81–99%) with high enantioselectivities (up to 96% ee) and spiro[4H-pyran-3,3-oxindole] derivatives (6a–l) in excellent yields (89–99%) with high ee (up to 95%). These aldol products and spiro-oxindoles constitute a core structural motif in a large number of pharmaceutically active molecules and natural products.
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Royal Society of Chemistry (RSC)ISSN Search the Publication Forum
2046-2069Keywords
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https://converis.jyu.fi/converis/portal/detail/Publication/104329116
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The authors would like to extend their sincere appreciation to the Researchers Supporting Project (RSP2022R427), King Saud University, Riyadh, Saudi Arabia.License
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