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Literature DB >> 23330983

Direct catalytic asymmetric alkynylation of ketoimines.

Liang Yin¹, Yasunari Otsuka, Hisashi Takada, Shinsuke Mouri, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki.

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.

Entities: Chemical

Mesh：

Substances：
Alkynes
Imines
Lewis Acids

Year: 2013 PMID： 23330983 DOI： 10.1021/ol3035609

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

Authors: Jessica Z Chan; Ahmet Yesilcimen; Min Cao; Yuyang Zhang; Bochao Zhang; Masayuki Wasa
Journal: J Am Chem Soc Date: 2020-09-11 Impact factor: 15.419

2. Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver Isoquinolines with α-Diaryl Tetrasubstituted Stereocenters.

Authors: Srimoyee Dasgupta; Jixin Liu; Clarissa A Shoffler; Glenn P A Yap; Mary P Watson
Journal: Org Lett Date: 2016-11-16 Impact factor: 6.005

Direct catalytic asymmetric alkynylation of ketoimines.

1. Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

2. Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver Isoquinolines with α-Diaryl Tetrasubstituted Stereocenters.

Review 3. Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions.

4. Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst.

5. Direct Enantioselective Addition of Alkynes to Imines by a Highly Efficient Palladacycle Catalyst.

6. Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.

7. Iterative addition of carbon nucleophiles to N,N-dialkyl carboxamides for synthesis of α-tertiary amines.