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

研究成果: Article › 査読

59 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	698-701
ページ数	4
ジャーナル	Organic Letters
巻	15
号	3
DOI	https://doi.org/10.1021/ol3035609
出版ステータス	Published - 2013 2月 1
外部発表	はい

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol3035609

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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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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

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