Synthesis and Reduction of 2,2-diaryl-1-nitroethylenes by using a chiral and a non chiral NADH model in the pyrrolopyridine series

Article abstract of DOI:10.1002/jhet.5570330435

Reduction of 2,2-diphenyl-1-nitroethylene (1) and 2-(2-pyridyl)-2-phenyl-1-nitroethylene (5) is achieved by using the NADH model in the pyrrolopyridine series 2a to give 2,2-diphenyl-1-nitroethane (3) and 2-(2-pyridyl)-2-phenyl-1-nitroethane (7) respectively in 40% yield. The asymmetric reduction of 2-(2-pyridyl)-2-phenyl-1-nitroethylene by the chiral NADH model 2b is studied. Thus, 2-(2-pyridyl)-2-phenyl-1-nitroethane (7) is obtained in 15 to 32% yield. The stereocontrol of the reduction proved to be dependent on the amount of magnesium ions.