Synthesis of chiral polydentate ligands and the use of their titanium complexes as pre-catalysts for the asymmetric trimethylsilylcyanation of benzaldehyde |
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| Authors: | Yu N Belokon D A Chusov T V Skrupskaya D A Bor’kin L V Yashkina K A Lyssenko M M Il’in T V Strelkova G I Timofeeva A S Peregudov M North |
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| Institution: | (1) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation;(2) School of Natural Sciences and University Research Centre in Catalysis and Intensified Processing, University of Newcastle, Bedson Building, UK, Newcastle Upon Tyne |
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| Abstract: | A number of polydentate ligands based on enantiomerically pure binaphthol have been synthesized. The ligand complexes with
titanium isopropoxide were used as catalysts for the asymmetric addition of trimethylsilyl cyanide to benzaldehyde. A fragment
with axial chirality is responsible for the configuration of O-trimethylsilyl cyanohydrin product. In the case of the optimum ligand based on (R)-binaphthol and (S)-leucinol, an enantiomeric excess of 86% and quantitative yield were achieved in 4 h.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1946–1953, September, 2008. |
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| Keywords: | asymmetric catalysis titanium complexes cyanohydrins trimethylsilyl cyanide benzaldehyde |
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