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

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

Journal Name: Letters in Organic Chemistry

Volume 7 , Issue 2 , 2010

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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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Article Details

VOLUME: 7
ISSUE: 2
Year: 2010
Page: [114 - 120]
Pages: 7
DOI: 10.2174/157017810790796354
Price: $58

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