2023
DOI: 10.1039/d3sc00118k
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Enantio- and diastereodivergent synthesis of fused indolizines enabled by synergistic Cu/Ir catalysis

Abstract: Highly diastereo-/enantioselective assembly of 2,3-fused indolizine derivatives could be easily available through a cascade allylation/Friedel-Crafts type reaction enabled by a synergistic Cu/Ir catalysis. This designed protocol provides an unprecedented and...

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Cited by 19 publications
(10 citation statements)
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“…More recently, utilizing the synergistic Cu/Ir-catalyzed asymmetric allylic alkylation and intramolecular cyclization strategy, Wang, Dong, Dang, and co-workers reported the experimental and computational development of a stereodivergent synthesis to access the enantioenriched azepino­[3,4,5- cd ]­indoles and fused indolizines (Figure ). , Our DFT computational mechanistic studies also emphasize the decisive function of dispersion interactions in the stereocontrolling C­(sp 3 )–C­(sp 3 ) bond-coupling step through allylic alkylation. Meanwhile, the Lewis acid or proton acid undertakes an indispensable promoting effect in the following cyclization process.…”
Section: Dispersion Interactions In Stereodivergent Annulation Via Cu...mentioning
confidence: 99%
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“…More recently, utilizing the synergistic Cu/Ir-catalyzed asymmetric allylic alkylation and intramolecular cyclization strategy, Wang, Dong, Dang, and co-workers reported the experimental and computational development of a stereodivergent synthesis to access the enantioenriched azepino­[3,4,5- cd ]­indoles and fused indolizines (Figure ). , Our DFT computational mechanistic studies also emphasize the decisive function of dispersion interactions in the stereocontrolling C­(sp 3 )–C­(sp 3 ) bond-coupling step through allylic alkylation. Meanwhile, the Lewis acid or proton acid undertakes an indispensable promoting effect in the following cyclization process.…”
Section: Dispersion Interactions In Stereodivergent Annulation Via Cu...mentioning
confidence: 99%
“…Our quantum-mechanical modeling highlighted that ligand–ligand, ligand–substrate, and substrate–substrate dispersion interactions play significant roles in stereocontrol of these important asymmetric reactions (Figure ). In this Account, we present several examples to showcase the resultant stereoinduction models for the key C­(sp 3 )–C­(sp 3 ) bond-forming transition states and highlight the important effect of attractive dispersion in stereoinduction. ,, …”
Section: Introductionmentioning
confidence: 99%
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“…Among various synthetic methods to chiral pyroglutamic acids and their derivatives, the asymmetric conjugated addition between glycinates and α,β-unsaturated esters followed by lactamization is a highly straightforward strategy. 3 In the past few decades, the development of asymmetric 1,4-conjugate additions of glycine imine esters to various α,β-unsaturated carbonyl compounds has gained considerable attention, and various catalysts including alkaline-earth-metals, 4 transition metals, 5 phase transfer catalysts, 6 and Brønsted base catalysts 7 were used to produce chiral pyroglutamic acids and their corresponding derivatives both in high yields and selectivities. Soloshonok 8 and co-workers have developed a type of Ni( ii ) complex of glycine Schiff bases for the asymmetric synthesis of β-substituted pyroglutamic acids via Michael additions of chiral oxazolidinone derived Michael acceptors.…”
Section: Introductionmentioning
confidence: 99%