Direct Catalytic Asymmetric Alkynylation of Ketoimines

Direct Catalytic Asymmetric Alkynylation of Ketoimines

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...

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Veröffentlicht in:Organic letters 2013-02, Vol.15 (3), p.698-701
Hauptverfasser: Yin, Liang, Otsuka, Yasunari, Takada, Hisashi, Mouri, Shinsuke, Yazaki, Ryo, Kumagai, Naoya, Shibasaki, Masakatsu
Format: Artikel
Sprache:eng
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Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Imines - chemistry
Lewis Acids - chemistry
Stereoisomerism
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container_end_page 701
container_issue 3
container_start_page 698
container_title Organic letters
container_volume 15
creator Yin, Liang
Otsuka, Yasunari
Takada, Hisashi
Mouri, Shinsuke
Yazaki, Ryo
Kumagai, Naoya
Shibasaki, Masakatsu
description 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.
doi_str_mv 10.1021/ol3035609
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subjects Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Imines - chemistry
Lewis Acids - chemistry
Stereoisomerism
title Direct Catalytic Asymmetric Alkynylation of Ketoimines
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