6533b7d8fe1ef96bd12697a3
RESEARCH PRODUCT
Mixed Dialkylaluminum Chlorides and Mixed Trimethylorganoaluminates in Chemoselective 1,4 Addition Reactions to Alkylidene Malonic Acid Diethyl Ester
Steffen MaasHorst Kunzsubject
chemistry.chemical_classificationAddition reactionchemistry.chemical_compoundChemistryHydrideReagentArylMichael reactionChemoselectivityMalonic acidMedicinal chemistryAlkyldescription
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 |
|---|---|---|---|---|
| 2000-04-01 | Journal für praktische Chemie |