Asymmetric Hydrocyanation of Nitroolefins Catalyzed by an Aluminum(III) Salen Complex. Issue 9 (1st August 2014)

• Record Type: Journal Article
• Authors: Jakhar, Ajay; Sadhukhan, Arghya; Khan, Noor‐ul H.; Saravanan, S.; Kureshy, Rukhsana I.; Abdi, Sayed H. R.; Bajaj, Hari C.
• Is Part Of: ChemCatChem. Volume 6:Issue 9(2014:Sep.)
• Page Start: 2656
• Page End: 2661
• Publication Date: 2014-08-01
• Subjects: Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201402373
• Languages: English
• ISSNs: 1867-3880

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Chiral Al^III salen complexes were synthesized and used as catalysts for the asymmetric hydrocyanation of nitroolefins using 4‐phenylpyridine <italic>N</italic>‐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 Al^III salen complex and additive, NMR and IR spectroscopic studies revealed that 4‐phenylpyridine <italic>N</italic>‐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.</p> </abstract>