Conjugate addition of tris(phenylthio)methyl-lithium to αβ-unsaturated ketones. Synthesis of γ-keto-esters

Author(s):  
Abdul-Rahman B. Manas ◽  
Robin A. J. Smith
1974 ◽  
Vol 52 (11) ◽  
pp. 2157-2164 ◽  
Author(s):  
Stuart Nicholas Huckin ◽  
Larry Weiler

The dianion of methyl acetoacetate reacts with ketones and aldehydes to yield δ -hydroxy-β-keto esters. These hydroxy esters can be dehydrated to the corresponding γ,δ-unsaturated-β-keto esters which are useful in annelation reactions to form cyclic β-keto esters. The dianion of methyl acetoacetate does not appear to undergo conjugate addition to simple α,β-unsaturated ketones, instead only carbonyl addition occurs.


1980 ◽  
Vol 45 (15) ◽  
pp. 3053-3061 ◽  
Author(s):  
Jeffrey Schwartz ◽  
Denise B. Carr ◽  
Robert T. Hansen ◽  
Fabian M. Dayrit

2017 ◽  
Vol 15 (19) ◽  
pp. 4191-4198 ◽  
Author(s):  
Haojiang Wang ◽  
Yifeng Wang ◽  
Cheng Zhang ◽  
Yidong Jiang ◽  
Mingming Chu ◽  
...  

A highly enantioselective conjugate addition of 2-substituted benzofuran-3(2H)-ones to α,β-unsaturated ketones promoted by chiral copper complexes has been developed.


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