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
Schlagworte:
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Imines - chemistry
Lewis Acids - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3035609