155697-97-5Relevant academic research and scientific papers
Direct transformation of dialkyl sulfates into alkyllithium reagents by a naphthalene-catalysed lithiation
Guijarro, David,Guillena, Gabricia,Mancheno, Balbino,Yus, Miguel
, p. 3427 - 3436 (1994)
The lithiation of primary and secondary dialkyl sufates with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in THF at -78°C leads to the corresponding alkyllithium reagents (1:2 molar ratio) which react with different electrophiles, mainly carbonyl compounds, to yield after hydrolysis, the expected coupling products. This methodology represents an indirect way to transform alcohols into organolithium compounds through the corresponding dialkyl sulfates. When the same procedure is applied to five or six member cyclic sulfates (derived from 1,2- or 1,3-diols) only products arising from a β- or γ-elimination process (giving olefins or cyclopropanes), respectively, are obtained.
Synthesis of substituted cyclopropanes from 1,3-diols through the corresponding cyclic sulfates
Guijarro, David,Yus, Miguel
, p. 11445 - 11456 (2007/10/02)
The reaction of different cyclic sulfates 2 (easily prepared from the corresponding 1,3-diols 1 following the Sharpless methodology) with an excess of lithium powder and a catalytic amount of DTBB (5 mol %) leads to the corresponding substituted cyclopropanes 3 through a γ-elimination process, the sulfate ion acting as leaving group.
