Synthesis of Allyl Sulfoxides from Allylsilanes via Silyl Sulfinates

Tetrahedron Letters 2015
Agnese Stikute, Vilnis Peipiņš, Māris Turks

Allylsilanes underwent sila-ene reaction with sulfur dioxide in the presence of Lewis acid catalysts. The obtained Vogel’s silyl sulfinates were found to act as sulfinyl transfer agents in reactions with aryl, heteroaryl, alkyl, and allyl Grignard reagents proceeding with the expulsion of the trialkylsilyloxy group to give allyl sulfoxides in up to 83% yield. The nucleophilic attack of Grignard reagents was accelerated in toluene and in the presence of LiCl or ZnCl2 as Lewis acidic additives. The developed method allows the transformation of allylsilanes into allyl sulfoxides.

Keywords
Sila-ene reaction, Sulfur dioxide, Silyl sulfinates, Trimethylsilyl 2-methylprop-2-ene-1-sulfinate, Sulfoxides, Grignard reagents
DOI
10.1016/j.tetlet.2015.06.018
Hyperlink
http://www.sciencedirect.com/science/article/pii/S0040403915009995

Stikute, A., Peipiņš, V., Turks, M. Synthesis of Allyl Sulfoxides from Allylsilanes via Silyl Sulfinates. Tetrahedron Letters, 2015, Vol.56, Iss.31, pp.4578-4581. ISSN 0040-4039. Available from: doi:10.1016/j.tetlet.2015.06.018

Publication language
English (en)