Direct catalytic asymmetric alkynylation of ketoimines

Liang Yin, Yasunari Otsuka, Hisashi Takada, Shinsuke Mouri, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

An efficient protocol for direct catalytic alkynylation of ketoimines is described. The simultaneous activation of a soft Lewis basic terminal alkyne and a ketoimine bearing a thiophosphinoyl group by soft Lewis acid Cu(I) is crucial for high conversion. The reaction can be rendered asymmetric with a chiral bisphosphine ligand (S,S)-Ph-BPE.

Original languageEnglish
Pages (from-to)698-701
Number of pages4
JournalOrganic Letters
Volume15
Issue number3
DOIs
Publication statusPublished - Feb 1 2013
Externally publishedYes

Fingerprint

Bearings (structural)
Lewis Acids
Alkynes
alkynes
Chemical activation
activation
Ligands
ligands
acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Yin, L., Otsuka, Y., Takada, H., Mouri, S., Yazaki, R., Kumagai, N., & Shibasaki, M. (2013). Direct catalytic asymmetric alkynylation of ketoimines. Organic Letters, 15(3), 698-701. https://doi.org/10.1021/ol3035609

Direct catalytic asymmetric alkynylation of ketoimines. / Yin, Liang; Otsuka, Yasunari; Takada, Hisashi; Mouri, Shinsuke; Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu.

In: Organic Letters, Vol. 15, No. 3, 01.02.2013, p. 698-701.

Research output: Contribution to journalArticle

Yin, L, Otsuka, Y, Takada, H, Mouri, S, Yazaki, R, Kumagai, N & Shibasaki, M 2013, 'Direct catalytic asymmetric alkynylation of ketoimines', Organic Letters, vol. 15, no. 3, pp. 698-701. https://doi.org/10.1021/ol3035609
Yin L, Otsuka Y, Takada H, Mouri S, Yazaki R, Kumagai N et al. Direct catalytic asymmetric alkynylation of ketoimines. Organic Letters. 2013 Feb 1;15(3):698-701. https://doi.org/10.1021/ol3035609
Yin, Liang ; Otsuka, Yasunari ; Takada, Hisashi ; Mouri, Shinsuke ; Yazaki, Ryo ; Kumagai, Naoya ; Shibasaki, Masakatsu. / Direct catalytic asymmetric alkynylation of ketoimines. In: Organic Letters. 2013 ; Vol. 15, No. 3. pp. 698-701.
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