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Synthesis of chiral polydentate ligands and the use of their titanium complexes as pre-catalysts for the asymmetric trimethylsilylcyanation of benzaldehyde

Lookup NU author(s): Professor Michael North

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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.

Publication metadata

Author(s): Belokon YN, Chusov DA, Skrupskaya TV, Bor'kin DA, Yashkina LV, Lyssenko KA, Il'in MM, Strelkova TV, Timofeeva GI, Peregudov AS, North M

Publication type: Article

Publication status: Published

Journal: Russian Chemical Bulletin

Year: 2008

Volume: 57

Issue: 9

Pages: 1981-1988

ISSN (print): 1066-5285

ISSN (electronic): 1573-9171

Publisher: Springer

URL: http://dx.doi.org/10.1007/s11172-008-0266-6

DOI: 10.1007/s11172-008-0266-6

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