Direct catalytic asymmetric alkynylation of ketoimines

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

doi:10.1021/ol3035609

Direct catalytic asymmetric alkynylation of ketoimines

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

Research output: Contribution to journal › Article › peer-review

53 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 language	English
Pages (from-to)	698-701
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	3
DOIs	https://doi.org/10.1021/ol3035609
Publication status	Published - 2013 Feb 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3035609

Cite this

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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.",

author = "Liang Yin and Yasunari Otsuka and Hisashi Takada and Shinsuke Mouri and Ryo Yazaki and Naoya Kumagai and Masakatsu Shibasaki",

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T1 - Direct catalytic asymmetric alkynylation of ketoimines

AU - Yin, Liang

AU - Otsuka, Yasunari

AU - Takada, Hisashi

AU - Mouri, Shinsuke

AU - Yazaki, Ryo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2013/2/1

Y1 - 2013/2/1

N2 - 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.

AB - 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.

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Direct catalytic asymmetric alkynylation of ketoimines

Abstract

ASJC Scopus subject areas

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