Enantioselective O-acetylcyanation/cyanoformylation of aldehydes using catalysts with built-in crown ether-like motif in chiral macrocyclic V(V) salen complexes |
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Authors: | Noor-ul H. Khan Arghya SadhukhanNabin C. Maity Rukhsana I. KureshySayed H.R. Abdi S. SaravananHari C. Bajaj |
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Affiliation: | Discipline of Inorganic Materials and Catalysis, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific and Industrial Research (CSIR), G. B. Marg, Bhavnagar 364 002, Gujarat, India |
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Abstract: | Chiral macrocyclic V(V) salen complexes 1a-f derived from macrocyclic ligands obtained by the reaction of 1R,2R-(−) diaminocyclohexane/(1R,2R)-(+)-1,2-diphenylethylenediamine with bis-aldehydes 2 and 3 were synthesized and used as efficient catalysts in asymmetric cyanation reactions. The V(V) catalysts demonstrated excellent performance (product yields and ees up to 99%) with potassium cyanide (KCN) and sodium cyanide (NaCN). The catalytic system also performed very well with a safer source of cyanide-ethyl cyanoformate to give cyanohydrin carbonates in excellent yield and ee (up to 97%). The V(V) macrocyclic salen complex 1b retained its performance at multi-gram level and was conveniently recycled for a number of times. |
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Keywords: | Asymmetric O-acetylcyanohydrin Cyanohydrin carbonate Macrocyclic salen V(V) complexes Aldehydes Enantioselective |
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