Mn(III) salen complexes-catalyzed enantioselective addition of trimethyl silylcyanide to N-benzylimines in the presence of 4-phenyl pyridine-N-oxide as an additive

Abstract

Chiral monomeric and dimeric Mn(III) salen complexes viz., [( S,S)- N,N′-bis(3,5-di- tert-butylsalicylidene)-1,2-cyclohexanediaminato manganese(III) chloride and 5,5-methylene di-[( S,S)-{ N-(3- tert-butyl salicylidine)- N′-(3′,5′-di- tert-butyl salicylidene)}-1,2-cyclohexanediaminato manganese(III) chloride were used as catalysts for the highly enantioselective Strecker reaction of various imines (derived by the condensation of aldehydes and amine) with TMSCN as a source of cyanide in toluene. Excellent yield (95%) of α-amino nitrile with ee >99% was achieved when N-(2-methoxybenzylidine)-1-phenylmethanamine was used as a substrate and 4-phenyl pyridine-N-oxide (4-PPNO) as an additive at −55 °C in 28 h. The dimeric catalyst was found to be more reactive and enantioselective than the monomeric catalyst. The chiral dimeric catalyst used in the present study was recoverable and recyclable several times with retention of its performance.