Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides

Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

研究成果: ジャーナルへの寄稿記事

113 引用 (Scopus)

抄録

Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides under proton transfer conditions is described. Soft Lewis acid/hard Brønsted base cooperative catalysis is crucial for simultaneous activation of terminal alkynes and thioamides, affording the β-alkynylthioamides in a highly enantioselective manner. Control experiments suggested that the intermediate copper thioamide enolate can work as Brønsted base to drive the catalytic cycle via proton transfer. The divergent transformation of the thioamide functionality highlights the synthetic utility of the alkynylation products.

元の言語英語
ページ(範囲)10275-10277
ページ数3
ジャーナルJournal of the American Chemical Society
132
発行部数30
DOI
出版物ステータス出版済み - 8 4 2010

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Thioamides
Proton transfer
Alkynes
Catalysis
Protons
Chemical activation
Copper
Lewis Acids
Acids
Experiments

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

これを引用

Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides. / Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu.

:: Journal of the American Chemical Society, 巻 132, 番号 30, 04.08.2010, p. 10275-10277.

研究成果: ジャーナルへの寄稿記事

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AB - Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides under proton transfer conditions is described. Soft Lewis acid/hard Brønsted base cooperative catalysis is crucial for simultaneous activation of terminal alkynes and thioamides, affording the β-alkynylthioamides in a highly enantioselective manner. Control experiments suggested that the intermediate copper thioamide enolate can work as Brønsted base to drive the catalytic cycle via proton transfer. The divergent transformation of the thioamide functionality highlights the synthetic utility of the alkynylation products.

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