Synthesis of (E)-α,β-unsaturated ketones by hydrostannylation-Stille tandem reaction of alkylarylacetylenes with acyl chlorides

2010 ◽  
Vol 34 (10) ◽  
pp. 559-561 ◽  
Author(s):  
Jianying Li ◽  
Yan Yu ◽  
Wenyan Hao ◽  
Mingzhong Cai
Keyword(s):  
Tandem Reaction ◽  
Acyl Chlorides ◽  
Unsaturated Ketones

Acylation du (cyclopropylméthyl)triméthylsilane. Une nouvelle voie d'accès aux énones non conjuguées

1981 ◽  
Vol 59 (5) ◽  
pp. 802-806 ◽  
Author(s):  
M. Grignon-Dubois ◽  
J. Dunoguès ◽  
R. Calas
Keyword(s):  
Saturated Hydrocarbon ◽  
Chloroacetyl Chloride ◽  
Competitive Reaction ◽  
Acyl Chlorides ◽  
Unsaturated Ketones ◽  
Unsaturated Acyl ◽  
Catalytic Role ◽  
Convenient Route ◽  
Allylic Cleavage

Acylation of (cyclopropylmethyl)trimethylsilane using RCOCl/AlCl3 (R: saturated hydrocarbon group) constitutes a mild, convenient route to β,γ-unsaturated ketones free from the conjugated isomers. With α,β-unsaturated acyl chlorides a competitive reaction between the C—H and C—Si allylic cleavage is observed whereas chloroacetyl chloride affords the γ,δ-ethylenic corresponding ketone. A mechanism involving the catalytic role of HCl in the formation of β,γ-unsaturated and chloroketones is proposed.

Environmentally benign access to isoindolinones: synthesis, separation and resource recycling

2020 ◽  
Vol 22 (9) ◽  
pp. 2873-2878
Author(s):  
Weiwei Guo ◽  
Qi Zhang ◽  
Yang Cao ◽  
Kaihua Cai ◽  
Shengyong Zhang ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Tandem Reaction ◽  
Unsaturated Ketones ◽  
Resource Recycling

We have developed a green and facile approach for the straightforward installation of isoindolinone skeletons via a tandem reaction of 2-cyanobenzaldehydes and α,β-unsaturated ketones/esters.

Efficiently diastereoselective synthesis of functionalized hydro-carbazoles by base-mediated tandem annulation of 1-(2-amino-aryl)prop-2-en-1-ones and sulfur ylide

2020 ◽  
Vol 7 (12) ◽  
pp. 1469-1473 ◽  
Author(s):  
Chengyuan Wang ◽  
Jiong Zhang ◽  
Zheyuan Wang ◽  
Xin-Ping Hui
Keyword(s):  
Tandem Reaction ◽  
Diastereoselective Synthesis ◽  
Unsaturated Ketones ◽  
Sulfur Ylide

The base-promoted [3 + 3]/[1 + 4] tandem reaction of tosyl-protected o-amino α,β-unsaturated ketones and crotonate-derived sulfur ylide is developed for efficiently diastereoselective synthesis of functionalized hydrocarbazoles.

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