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Tetraaryl-1,3-dioxolane-4,5-dimethanols as catalysts for the addition of trimethylsilyl cyanide to benzaldehyde and the oxirane ring

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Abstract

The synthesis of 1,2-, 1,3-, and 1,4-phenylene-bis[(4R,5R)-4,5-di(hydroxydiphenylmethyl)-1,3-dioxolane]s (ortho-, meta-, and para-bis-(R,R)-TADDOLs) and bis[4-{[(4R, 5R)-4,5-di(hydroxydiphenylmethyl)]-1,3-dioxolan-2-yl}phenyl]methane was carried out. The possibilities of the use of these compounds as catalysts for the C-C bond formation in the addition of Me3SiCN to benzaldehyde and the oxirane ring opening in cyclohexene oxide by Me3SiCN were investigated. The catalytic activity of different bis-(R, R)-TADDOLs in this series depends on their structure.

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Correspondence to Yu. N. Belokon’.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1451–1458, August, 2007.

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Belokon’, Y.N., Maleev, V.I., Gugkaeva, Z.T. et al. Tetraaryl-1,3-dioxolane-4,5-dimethanols as catalysts for the addition of trimethylsilyl cyanide to benzaldehyde and the oxirane ring. Russ Chem Bull 56, 1507–1514 (2007). https://doi.org/10.1007/s11172-007-0233-7

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  • DOI: https://doi.org/10.1007/s11172-007-0233-7

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