Ajay Jakhar, Arghya Sadhukhan, N. H. Khan
Sep 1, 2014
Citations
1
Influential Citations
18
Citations
Journal
ChemCatChem
Abstract
Chiral AlIII salen complexes were synthesized and used as catalysts for the asymmetric hydrocyanation of nitroolefins using 4‐phenylpyridine N‐oxide as an additive and trimethylsilyl cyanide (TMSCN) as a source of cyanide. An excellent yield of β‐nitronitrile (87 %) and enantioselectivity (90 %) were achieved if (2‐nitrovinyl)cyclohexane was used as a substrate at −15 °C in 16 h. To understand the interaction of the AlIII salen complex and additive, NMR and IR spectroscopic studies revealed that 4‐phenylpyridine N‐oxide acts both as an axial ligand and helps to activate the cyanide source TMSCN, which thereby increases the reactivity. A catalytic cycle was proposed based on the spectroscopic studies.