Reaction of C2-symmetrical dialkoxysilanes R1O-Si(R-2)(2)-OR1 with the twoVilsmeier-Haack complexes POCl3 center dot DMF and (CF3SO2)(2)O center dotDMF: An efficient one-step conversion to the corresponding formates R-1-OCHO

Authors
Cohen, Y Kotlyar, V Koeller, S Lellouche, JP
Citation
Y. Cohen et al., Reaction of C2-symmetrical dialkoxysilanes R1O-Si(R-2)(2)-OR1 with the twoVilsmeier-Haack complexes POCl3 center dot DMF and (CF3SO2)(2)O center dotDMF: An efficient one-step conversion to the corresponding formates R-1-OCHO, SYNLETT, (10), 2001, pp. 1543-1546
Citations number
33
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
10
Year of publication
2001
Pages
1543 - 1546
Database
ISI
SICI code
0936-5214(200110):10<1543:ROCDRW>2.0.ZU;2-L
Abstract
The two electrophilic Vilsmeier-Haack complexes POCl3. DMF 1 and (CF3SO2)(2 )O . DMF 2 react with C2-symmetrical dialkoxysilanes R1O-Si(R-2)(2)-OR1 (R- 1 = (-)-menthyl or 3 beta -cholesteryl, R-2 = Me, Ph or i-Pr: 5a-c/6a-c) af fording the formates R-1-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.