The Reaction Between Triethylaluminium and Methyl Isopropenyl Ketone

Lyons, A. R.; Catterall, E.

doi:10.1016/s0022-328x(00)87834-1

Cited by 8 publications

(2 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast, Lyons and Catterall reported just 1,2-addition upon treatment of methyl isopropenyl ketone with triethylaluminum in non-coordinating solvents (toluene) at room temperature. 14 No change in selectivity was observed upon raising the amount of the alane, yet an excess of enone led to polymerization. Similarly, benzalacetone (10) predominantly underwent 1,2-addition with triethylaluminum in benzene as shown by Baba (Scheme 2).…”

Section: Figurementioning

confidence: 99%

Selectivity Control in 1,2- and 1,4-Additions of Aluminum Organyls to Carbonyl Compounds

Zezschwitz¹

2008

Synthesis

View full text Add to dashboard Cite

Aluminum organyls are valuable reagents for carboncarbon bond formation as they can either be purchased at low prices or conveniently be prepared, for example, by hydro-or carboalumination of alkenes and alkynes. Although their application in reactions with a,b-unsaturated carbonyl compounds is rather limited, it creates a diverse picture concerning the selectivity of product formation which depends on several factors such as the type of organic residue, the conformation of the enone, the presence of additional functional groups and the donor ability of the solvent. This review describes issues of selectivity of such uncatalyzed transformations as well as conjugate additions catalyzed by achiral copper and nickel catalysts in which alanes can act similarly or even superiorly to the more common lithium or magnesium organyls. Moreover, the rapidly growing field of transition-metal-catalyzed asymmetric 1,2and 1,4-additions is reviewed, in which aluminum reagents can not only lead to enantioselective alkyl additions, thus substituting zinc organyls, but also afford introduction of aryl, alkenyl and alkynyl groups. 1 Introduction 2 Uncatalyzed Additions to a,b-Unsaturated Carbonyl Compounds 2.1 Regioselectivity with Plain Enones 2.2 Selective Conjugate Additions to Cyclic Enones 2.3 Conjugate Additions to Carboxylic Compounds 3 Racemic Copper-and Nickel-Catalyzed 1,4-Additions 4 Asymmetric Addition to Carbonyl Compounds 4.1 Enantioselective Conjugate Additions to Enones 4.2 Enantioselective 1,2-Additions 5 Conclusion

show abstract

Section: Figurementioning

confidence: 99%

Selectivity Control in 1,2- and 1,4-Additions of Aluminum Organyls to Carbonyl Compounds

Zezschwitz¹

2008

Synthesis

View full text Add to dashboard Cite

show abstract

“…Baba (77) reports that mainly 1,Zaddition occurs in the reaction between triethylaluminium and various /?-substituted vinyl ketones. Lyons (78) showed that the exothermic reaction between methyl isopropenyl ketone and triethylaluminium led to the yellow "ate"-complex which rearranged at ambient temperature to the carbonyl adduct. Yellow adducts were similarly obtained by Allen (60) between both methyl vinyl ketone and methyl isopropenyl ketone with triethylaluminium at ambient temperature.…”

Section: Reactions Between Vinyl Ketones and Ionic Initiatorsmentioning

confidence: 99%