Lewis Acid-Catalyzed One-Pot, Three-Component Route to Chiral 3,3‘-Bipyrroles
Organic Letters2008Vol. 10(7), pp. 1373–1376
Citations Over TimeTop 12% of 2008 papers
Sumit Dey, Chiranjib Pal, Debkumar Nandi, Venkatachalam S. Giri, M. Zaidlewicz, M. Krzemiński, Lidia Smentek, B. Andes Hess, Jacek Gawroński, Marcin Kwit, N.J. Babu, Ashwini Nangia, Parasuraman Jaisankar
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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