@article{20dfd1959727430f8fdfaa73b16d6230,
title = "Regio- and stereoselectivity of the 1,3-dipolar cycloaddition of azomethine ylides to (E)-3-(2-oxo-2-(pyren-1-yl)ethylidene)indolin-2-ones: A combined experimental and theoretical study",
abstract = "Functionalized oxindoles and pyrrolizidines form the central structural framework for numerous natural products with extensive biological and pharmacological applications. The requirement for high regio- and stereoselectivity is the main obstacle in the synthesis of such five-membered heterocycles. Multicomponent cycloaddition reactions often provide an efficient and straightforward approach for the preparation of specific regio- and stereoisomers. In this article, the regio- and stereochemistry of the polar [3 + 2]-cycloaddition (32CA) reaction of azomethine ylides prepared by the reaction of isatin derivatives and L-proline with a series of (E)-3-(2-oxo-2-(pyren-1-yl)ethylidene)indolin-2-ones was investigated by experimental and theoretical methods. Among the isatin and (E)-3-(2-oxo-2-(pyren-1-yl)ethylidene)indolin-2-one derivatives, a remarkable inversion of regioselectivity was observed in the 32CA reaction of azomethine ylide generated by the reaction of L-proline and 5-chloroisatin or N-methyl-5-chloroisatin with (E)-5-chloro-3-(2-oxo-2-(pyren-1-yl)ethylidene)indolin-2-one. The regio- and stereochemical assignment of the structures of the cycloaddition products was determined by one- and two-dimensional (1D&2D) homonuclear and heteronuclear correlation nuclear magnetic resonance spectroscopy. The molecular mechanism as well as the regio- and stereoselectivity of the cycloaddition were investigated by means of global and local reactivity indices and a density functional theory (DFT) and explained in detail on the basis of the transition state stabilities of the reactants.",
keywords = "DFT, Local reactivity, Multicomponent [3 + 2] cycloaddition, Natural product scaffold, Transition state",
author = "Hussein, {Essam M.} and Ziad Moussa and Uttam Pal and Alsantali, {Reem I.} and Alzahrani, {Abdullah Y.A.} and Obaid, {Rami J.} and Alzahrani, {Fawaz M.} and Al-Rooqi, {Munirah M.} and Alsharif, {Meshari A.} and {El Guesmi}, Nizar and Jassas, {Rabab S.} and {Shaheer Malik}, M. and Altass, {Hatem M.} and Pal, {Samir K.} and {Saha Dasgupta}, Tanusri and Ahmed, {Saleh A.}",
note = "Funding Information: The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through the Small Research Project under grant number (RGP.1/124/42). The authors would like to acknowledge the Deanship of Scientific Research at Umm Al-Qura University, for supporting this work by Grant code: 22UQU4350067DSR01. Also, the authors would like to extend their sincere appreciation to Taif University Researchers Supporting Project number (TURSP-2020/312), Taif University, Taif, Saudi Arabia. Dr. Ziad Moussa is grateful to the United Arab Emirates University (UAEU) of Al-Ain and to the Research Office for supporting the research developed in his laboratory (Grant no. G00003291). Funding Information: The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through the Small Research Project under grant number (RGP.1/124/42). The authors would like to acknowledge the Deanship of Scientific Research at Umm Al-Qura University, for supporting this work by Grant code: 22UQU4350067DSR01. Also, the authors would like to extend their sincere appreciation to Taif University Researchers Supporting Project number (TURSP-2020/312), Taif University, Taif, Saudi Arabia. Dr. Ziad Moussa is grateful to the United Arab Emirates University (UAEU) of Al-Ain and to the Research Office for supporting the research developed in his laboratory (Grant no. G00003291). Publisher Copyright: {\textcopyright} 2022 The Author(s)",
year = "2022",
month = jun,
doi = "10.1016/j.arabjc.2022.103855",
language = "English",
volume = "15",
journal = "Arabian Journal of Chemistry",
issn = "1878-5352",
publisher = "King Saud University",
number = "6",
}