Montmorillonite-K10 Catalyzed Addition OF Trimethylsilylcyanide (TMSCN) to Aldehydes.
作者:R. Somanathan、I. A. Rivero、Angeles Gama、A. Ochoa、G. Aguirre
DOI:10.1080/00397919808007179
日期:1998.6
Addition of trimethylsilyl cyanide (TMSCN) to aldehydes was catalyzed by Montmorillonite-K10, with subsequent reduction to beta-aminoalcohol.In recent years we have explored a number of methodologies for the preparation of beta-aminoalcohols(1-4), many of which are biologically active and are also versatile intermediates in organic synthesis as highlighted in a recent review article(5).A convenient route to these beta-aminoalcohols, is the addition of trimethylsilyl cyanide (TMSCN) to an aldehyde or ketone in the presence of a Lewis acid catalyst(6) and subsequent hydride reductions(7,8) to beta-aminoalcohol. Many different Lewis acid catalysts, such as Znl(2), AlCl3, BF3, and Ti(OiPr)(4), have been employed in this reaction. The drawback of this protocol is that the Lewis acid is soluble in the reaction media and very often the final silyloxycyanide is recovered from the reaction mixture by a short path vacuum distillation.