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Synlett 2001; 2001(10): 1543-1546
DOI: 10.1055/s-2001-18395
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Reaction of C2-Symmetrical Dialkoxysilanes R1O-Si(R2)2-OR1 with the two Vilsmeier-Haack Complexes POCl3 · DMF and (CF3SO2)2O · DMF: An Efficient One-Step Conversion to the Corresponding Formates R1-OCHO

Yariv Cohen* , Vadim Kotlyar, Sylvain Koeller, Jean-Paul Lellouche
  • *Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel; Fax +972(3)5351250; E-mail: lellouj§mail.biu.ac.il
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Publication Date:
27 September 2001 (online)

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The two electrophilic Vilsmeier-Haack complexes POCl3 · DMF 1 and (CF3SO2)2O · DMF 2 react with C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 (R1 = (-)-menthyl or 3β-cholesteryl, R2=Me, Ph or i-Pr: 5a-c/6a-c) affording the formates R1-OCHO 7 and 8 in medium to good yields depending on conditions. The scope and limitations of this novel one-step deprotection of C2-symmetrical silaketals to formates are described.

Vilsmeier-Haack complexes - protecting group interconversion - deprotection - formates - formylation