Direct Experimental Evidence for the Priority of Flexible Ligand Skeleton in Asymmetric Friedel-Crafts Alkylation of Indole with Nitroalkenes

Han      Liu; Neng-Dong      Wang; Da-Ming      Du

doi:10.2174/157017810790796354

Abstract

Direct experimental evidence for the priority of flexible ligand skeleton in asymmetric Friedel-Crafts alkylation was obtained through XRD analysis of flexible ligand/ZnCl2 complex, as well as synthesis of dihydroacridine-linked bis(oxazoline) ligands with planar rigid scaffold. A transition state model without NH … π interaction was proposed for the rigid ligands to interpret the inversion of absolute configuration.

Keywords: Rigid scaffold, flexible scaffold, diphenylamine, dihydroacridine, bis(oxazoline), Friedel-Crafts alkylation

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Letters in Organic Chemistry

Title: Direct Experimental Evidence for the Priority of Flexible Ligand Skeleton in Asymmetric Friedel-Crafts Alkylation of Indole with Nitroalkenes

Volume: 7 Issue: 2

Author(s): Han Liu, Neng-Dong Wang and Da-Ming Du

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Keywords: Rigid scaffold, flexible scaffold, diphenylamine, dihydroacridine, bis(oxazoline), Friedel-Crafts alkylation

Abstract: Direct experimental evidence for the priority of flexible ligand skeleton in asymmetric Friedel-Crafts alkylation was obtained through XRD analysis of flexible ligand/ZnCl2 complex, as well as synthesis of dihydroacridine-linked bis(oxazoline) ligands with planar rigid scaffold. A transition state model without NH … π interaction was proposed for the rigid ligands to interpret the inversion of absolute configuration.

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Liu Han, Wang Neng-Dong and Du Da-Ming, Direct Experimental Evidence for the Priority of Flexible Ligand Skeleton in Asymmetric Friedel-Crafts Alkylation of Indole with Nitroalkenes, Letters in Organic Chemistry 2010; 7 (2) . https://dx.doi.org/10.2174/157017810790796354