Synlett 2001; 2001(10): 1543-1546
DOI: 10.1055/s-2001-18395
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
27 September 2001 (online)

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.