title: Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates.
abstract: Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxylate is protected with a benzyl group, selective mono-reduction does not occur. Considering that furan-2,5-dicarboxylates did not give the corresponding mono-alcohol under the same conditions, the unprotected nitrogen atom of pyrrole apparently plays an important role in this selective mono-reduction.
authors: Department of Applied Chemistry, Kogakuin University.
authors: Eiko
authors: E
authors: Yasui
authors: Jyunpei
authors: J
authors: Tsuda
authors: Satoshi
authors: S
authors: Ohnuki
authors: Shinji
authors: S
authors: Nagumo
mesh_terms: D003998:Dicarboxylic Acids / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D003998:Dicarboxylic Acids; D011758:Pyrroles