A1 Journal article (refereed)
Cu(ii)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol reaction and Domino Knoevenagel Michael cyclization : a new highly efficient Lewis acid catalyst (2022)


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


JYU authors or editors


Publication details

All authors or editorsAl-Majid, Abdullah Mohammed; Alammari, Abdullah Saleh; Alshahrani, Saeed; Haukka, Matti; Islam, Mohammad Shahidul; Barakat, Assem

Journal or seriesRSC Advances

eISSN2046-2069

Publication year2022

Volume12

Issue number10

Pages range6149-6165

PublisherRoyal Society of Chemistry (RSC)

Publication countryUnited Kingdom

Publication languageEnglish

DOIhttps://doi.org/10.1039/d2ra00674j

Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/79897


Abstract

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.


Keywordscatalystsheterocyclic compounds


Contributing organizations


Ministry reportingYes

Reporting Year2022

JUFO rating1


Last updated on 2024-15-06 at 00:25