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RESEARCH PRODUCT
ChemInform Abstract: Mixed Dialkylaluminum Chlorides and Mixed Trimethylorganoaluminates in Chemoselective 1,4-Addition Reactions to Alkylidene Malonic Acid Diethyl Ester.
Steffen MaasHorst Kunzsubject
chemistry.chemical_classificationchemistry.chemical_compoundAddition reactionHydrideChemistryArylReagentMichael reactionOrganic chemistryGeneral MedicineMalonic acidAlkylConjugatedescription
Mixed alkyl-methyl- and aryl-methylorganoaluminum chlorides 6 were formed by reaction of methylaluminum dichloride with organolithium or Grignard compounds and used for chemoselective 1,4 addition of higher alkyl, aryl, alkenyl and alkinyl groups to alkylidine malonic esters 1 and 2. As an alternative, mixed trimethylorganoaluminates 7 can also be applied for these Michael addition reactions. For conjugate addition of alkenyl groups to alkylidene malonates 1 and 2, alkenyl diisopropylalanes 10 obtained from alkynes and diisopropylaluminum hydride proved the most efficient reagents. Using these novel mixed organoaluminum compounds, β-branched malonic (carboxylic) acid derivatives 3c, 8, 9 and 11 were obtained in good yields. The method offers a general access to β-branched carboxylic derivatives of quite diverse structure not dependent on the commercial availability of the organoluminum chlorides.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-06-03 | ChemInform |