303143-99-9Relevant academic research and scientific papers
A sulfoxide version of the Julia-Lythgoe olefination: A new method for the synthesis of olefins from carbonyl compounds and sulfoxides with carbon-carbon coupling
Satoh, Tsuyoshi,Hanaki, Noriko,Yamada, Noriko,Asano, Tohru
, p. 6223 - 6234 (2007/10/03)
Reaction of β-mesyloxy (or acetoxy) sulfoxides, derived from alkyl (or arylmethyl) phenyl sulfoxides and carbonyl compounds in two steps, with alkylmetals (n-BuLi, t-BuLi, or EtMgBr) at low temperature gave olefins in good to excellent yields. When the β-hydroxy sulfoxides derived from arylaldehydes were treated with mesyl chloride in the presence of triethylamine, the sulfoxides directly gave E-olefins in good yields. These reactions offer a sulfoxide version of the Julia-Lythgoe olefination. The reductive vicinal elimination was found to take place through the direct sulfoxide-metal exchange. The stereochemistry of the elimination was investigated and found to be stereospecific; however, the stereospecificity was found to be dependent on the substrates. (C) 2000 Elsevier Science Ltd.
