479414-01-2Relevant academic research and scientific papers
Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to acyclic aliphatic enones
Mizutani, Hirotake,Degrado, Sylvia J.,Hoveyda, Amir H.
, p. 779 - 781 (2007/10/03)
Cu-catalyzed enantioselective conjugate additions to acyclic aliphatic enones are reported. The resulting enolates may be functionalized intra- and intermolecularly, leading to the formation of an additional C-C bond. The utility of the present method is not limited to reactions involving Et2Zn; a variety of alkylzincs may be used. Moreover, many of the requisite substrates can be easily accessed through catalytic olefin cross metathesis. Copyright
Efficient Cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones
Degrado, Sylvia J.,Mizutani, Hirotake,Hoveyda, Amir H.
, p. 13362 - 13363 (2007/10/03)
The first examples of efficient catalytic asymmetric conjugate addition (ACA) of alkylzincs to trisubstituted cyclic enones is disclosed. These Cu-catalyzed reactions proceed efficiently with five- and seven-membered ring substrates to afford the desired products in ≥95% ee. Intermediate enolates can be trapped with alkyl halides to generate a quaternary stereogenic center. The requisite chiral ligand is prepared from commercially available materials and can be used in situ without further purification in the presence of commercial grade (CuOTf)2·PhMe. Copyright
