4071-57-2Relevant academic research and scientific papers
Regioselective Robinson annulation realized by the combined use of lithium enolates and aluminum tris(2,6-diphenylphenoxide) (ATPH)
Saito, Susumu,Shimada, Itsuro,Takamori, Yusuke,Tanaka, Michiaki,Maruoka, Keiji,Yamamoto, Hisashi
, p. 1671 - 1681 (2007/10/03)
Michael addition of lithium enolates derived from ketones to a variety of a, β-unsaturated ketones was realized in the presence of aluminum tris(2,6-diphenylphenoxide) (ATPH). In this reaction, ATPH can be used as a carbonyl protector of a, β-unsaturated carbonyl substrates upon complexation, which facilitates the regioselective 1,4-addition of lithium enolates to Michael acceptors. Similarly, dianions of β-dicarbonyl compounds undergo Michael addition smoothly using ATPH as an effective promoter of the reaction. Subsequent regioselective, intramolecular aldol condensation was also demonstrated, leading to bicyclic carbon ring systems. Such systems are difficult to obtain by the Robinson annulation usually performed in protic media.
Lewis Acid Catalysed Michael-type Addition. A New Regio- and Diastereoselective Annulation Method using Methyl Vinyl Ketone
Duhamel, Pierre,Dujardin, Gilles,Hennequin, Laurent,Poirier, Jean-Marie
, p. 387 - 396 (2007/10/02)
A new annulation method is presented, involving a boron trifluoride catalysed Michael addition of trialkylsilyl enol ethers to methyl vinyl ketone (MVK) in the presence of a hydroxylic compound.This methodology allows regiospecific 3-oxobutylation of eith
A CONVENIENT PROCEDURE FOR CARBOXYLATION-ROBINSON ANNULATIONS OF KETONES USING TRIETHYLAMINE BASE IN THE PRESENCE OF MAGNESIUM CHLORIDE
Olsen, Richard S.,Fataftah, Zakaria A.,Rathke, Michael W.
, p. 1133 - 1140 (2007/10/02)
Carboxylation of ketones with carbon dioxide in the presence of magnesium chloride and triethylamine followed by reaction with methyl vinyl ketone gives satisfactory yields of Michael and Robinson annulation products.
