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Issue 16, 2019
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A chiral bicyclic skeleton-tethered bipyridine–Zn(OTf)2 complex as a Lewis acid: enantioselective Friedel–Crafts alkylation of indoles with nitroalkenes

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Abstract

A conformationally rigid chiral bicyclic skeleton tethered bipyridine–Zn(OTf)2 complex facilitated the enantioselective Friedel–Crafts alkylation of indoles with trans-β-nitroarylalkenes in an enantioselective manner at elevated temperature. Indoles reacted smoothly with β-nitroarylalkenes to generate the corresponding 3-(2-nitroalkyl)indoles in good to excellent yields (up to 94%) with moderate to excellent enantioselectivities (up to 91%). The stereochemical outcome of the product from indole and trans-β-nitrostyrene in the presence of the CRCB tethered bipyridine–Zn(OTf)2 complex and the DFT calculation of the CRCB tethered bipyridine–Zn:trans-β-nitrostyrene complex support the si-face attack of indole on trans-β-nitrostyrene.

Graphical abstract: A chiral bicyclic skeleton-tethered bipyridine–Zn(OTf)2 complex as a Lewis acid: enantioselective Friedel–Crafts alkylation of indoles with nitroalkenes

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Publication details

The article was received on 06 Mar 2019, accepted on 28 Mar 2019 and first published on 28 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00545E
Org. Biomol. Chem., 2019,17, 4077-4086

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    A chiral bicyclic skeleton-tethered bipyridine–Zn(OTf)2 complex as a Lewis acid: enantioselective Friedel–Crafts alkylation of indoles with nitroalkenes

    K. Venkatanna, S. Yeswanth Kumar, M. Karthick, R. Padmanaban and C. Ramaraj Ramanathan, Org. Biomol. Chem., 2019, 17, 4077
    DOI: 10.1039/C9OB00545E

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