TaCl5-silicagel and TaCl5 as new Lewis acid systems for selective tetrahydropyranylation of alcohols and thioacetalisation, trimerisation and aldolisation of aldehydes.

Chandrasekhar, S. ; Takhi, Mohamed ; Ravindra Reddy, Y. ; Mohapatra, Suchismita ; Rama Rao, C. ; Venkatram Reddy, K. (1997) TaCl5-silicagel and TaCl5 as new Lewis acid systems for selective tetrahydropyranylation of alcohols and thioacetalisation, trimerisation and aldolisation of aldehydes. Tetrahedron, 53 (44). pp. 14997-15004. ISSN 00404020

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Official URL: http://doi.org/10.1016/S0040-4020(97)01051-X

Related URL: http://dx.doi.org/10.1016/S0040-4020(97)01051-X

Abstract

TaCl5 adsorbed on silicagel has been utilized for the first time as Lewis acid catalyst for protection of aldehydes and alcohols as thiocetals and THP ethers respectively. Similarly TaCl5 has been exploited as an useful Lewis acid for chemoselective trimerisation and/or aldolisation of aldehydes. Very active Lewis acid catalyst system comprising of TaCl5-silicagel has been utilized for thioacetalisation of aldehydes and tetrahydropyranylation of alcohols. Similarly TaCl5 alone was exploited as good Lewis acid for selective trimerisation and/or aldolisation of aldehyde which is solvent dependent.

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