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...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2013-02, Vol.15 (3), p.698-701
Main Authors: Yin, Liang, Otsuka, Yasunari, Takada, Hisashi, Mouri, Shinsuke, Yazaki, Ryo, Kumagai, Naoya, Shibasaki, Masakatsu
Format: Article
Language:English
Subjects:
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Imines - chemistry
Lewis Acids - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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