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Published on: November 9, 2019
Lewis acid-catalyzed one-pot, three-component route to chiral 3,3'-bipyrroles
Sumit Dey1, Churala Pal, Debkumar Nandi
1Department of Chemistry, Indian Institute of Chemical Biology (Unit of CSIR), Jadavpur, Calcutta 700 032, India.
Abstract:
3,3'-Bipyrroles 3 could be synthesized using a double Michael addition reaction involving diaroyl acetylene 1 and the appropriate 1,3-dicarbonyls 2 using ammonium acetate as a nitrogen source. The axial chirality of bipyrrole was anticipated from the X-ray crystal structure and DFT calculations and confirmed by separating the racemates on a chiral column and subsequent CD spectra of the enantiomers. The absolute configuration of the enantiomers was achieved by theoretical CD spectra calculation using the ZINDO method.
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