Synthesis of a Chiral 3,3′-Di- tert -butyl-2,2′-bipyrrole |
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Authors: | Pawel Skowronek and David A Lightner |
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Abstract: | Diethyl 3,3′-di-tert-butyl-4,4′-dimethyl-2,2′-bipyrrole-5,5′-dicarboxylate was synthesized in four steps from ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate. The CH2 hydrogens of the ethyl ester groups of the former are diastereotopic in the 1H-NMR, consistent with axial chirality of the bipyrrole and restricted rotation about the 2,2′-bipyrrole bond, due to the
tert-butyl groups. An X-ray structure of the crystalline target compound shows the pyrrole rings are twisted out of coplanarity
by 84.5°. |
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