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Synthesis and diels-alder reactions of (S)-3-chloro and (S)-3-ethyl-2-p-tolylsulfinyl-1,4-benzoquinones

✍ Scribed by M.Carmen Carreño; José L.García Ruano; Miguel A. Toledo; Antonio Urbano


Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
378 KB
Volume
35
Category
Article
ISSN
0040-4039

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Diels-Alder reactions of [(S)R]-(1E,3E)-
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## Diels-Alder reactions of [(S)R]-(1E,3E )-l-p-tolylsulfinyl-l,3-pentadiene with 1-pyrrolidinyl-l-cyclohexene and methyl acrylate evidenced: i) low reactivity of the diene regardless of the electronic character of the dienophile (high pressures were always required); ii) a complete regio-and endo

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Enantiomerically pure (S)S-(p-tolylsulfinyl)-l,4-benzoquinones with alkyl and methoxy substituents at C-2 and/or C-3 are synthesized by CAN oxidation of adequately substituted (S)S-(p-tolylsulfinyl)-l,4-dimethoxyaromatic precursors 2 or 3. These compounds were obtained by ortho-directed metallation