Lewis acid-catalyzed one-pot, three-component route to chiral 3,3'-bipyrroles.
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.
Dey
Sumit
S
Department of Chemistry, Indian Institute of Chemical Biology (Unit of CSIR), Jadavpur, Calcutta 700 032, India.
Pal
Churala
C
Nandi
Debkumar
D
Giri
Venkatachalam Sesha
VS
Zaidlewicz
Marek
M
Krzeminski
Marek
M
Smentek
Lidia
L
Hess
B Andes
BA
Gawronski
Jacek
J
Kwit
Marcin
M
Babu
N Jagadeesh
NJ
Nangia
Ashwini
A
Jaisankar
Parasuraman
P
D002384:Catalysis; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D011758:Pyrroles