β-Trifluoromethyl-α-functionalized-vinyl sulfides as a potential synthetic intermediate

Takeshi Hanamoto, Ryoko Anno, Kenji Yamada, Kousuke Ryu, Ryoko Maeda, Kazuya Aoi, Hiroshi Furuno

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12 Citations (Scopus)

Abstract

The β-(trifluoromethyl)vinyl sulfides on treatment with n-BuLi/TMEDA at -78 °C were readily lithiated at an α-position of the sulfanyl group, and the generated β-trifluoromethyl-α-sulfanylvinyl anions were reacted with a variety of electrophiles to give the corresponding β-trifluoromethyl-α-functionalized-vinyl sulfides 4aa-4aq in good to excellent yields. The reactivity of some products has been examined. The palladium-catalyzed cross-coupling reaction as well as homo-coupling reaction of 4af provided the corresponding products in good yields, respectively. The Diels-Alder reaction of cyclic dienes and 14 derived from 4ao provided the desired six-membered cyclic products with high endo-trifluoromethyl group selectivity.

Original languageEnglish
Pages (from-to)2757-2765
Number of pages9
JournalTetrahedron
Volume65
Issue number14
DOIs
Publication statusPublished - Apr 4 2009

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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