Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes |
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Institution: | 1. Department of Pharmaceutics, School of Pharmacy, Jiangsu University, Zhenjiang, China;2. Department of Clinical Pharmacy, Affiliated Hospital of Jiangsu University, Zhenjiang, China;3. Institute of Green Chemistry and Chemical Technology, Jiangsu University, Zhenjiang, China;4. Intelligent Medical Research Center, Institute of Automation, Chinese Academy of Sciences, Beijing, China |
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Abstract: | Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino-1,7,7-trimethylbicyclo2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes have been studied with NMR techniques. Among them the complex with the Schiff base obtained from 2-hydroxy-3-isopropylbenzaldehyde, is the most selective catalyst for the cyanosilylation of aliphatic, alicyclic, aromatic, and heteroaromatic aldehydes. The highest enantioselectivity, >99%, was achieved for the addition of trimethylsilyl cyanide to cinnamaldehyde. |
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