72476-00-7Relevant academic research and scientific papers
ON THE USE OF beta PHENYLSULFINYL- alpha , beta -UNSATURATED CARBONYL DIENEOPHILES IN DIELS-ALDER REACTIONS.
Danishefsky,Harayama,Singh
, p. 7008 - 7012 (1979)
The use of beta -phenylsulfinyl- alpha , beta -unsaturted carbonyl dieneophiles as synthetic equivalents of alpha , beta -ethynyl carbonyl systems has been demonstrated. The sulfoxides were prepared by oxidation of the sulfides, which in turn were obtained from the beta -dicarbonyl systems by standard methods. A key feature of the scheme is that the phenylsulfinyl group does not compete with the carbonyl function in determining the regiochemistry of cycloaddition with the highly nucleophilic trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene. Application of the methodology to the synthesis of the disodium prephenate dimethyl acetals is described.
