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Synfacts 2014; 10(1): 0042
DOI: 10.1055/s-0033-1340436
DOI: 10.1055/s-0033-1340436
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Cu-Catalyzed Asymmetric 1,6-Conjugate Addition of Dialkylzinc
Magrez-Chiquet M, Morin MS. T, Wencel-Delord J, Amraoui SD, Baslé O, Alexakis A, Crévisy C, * Mauduit M. * Ecole Nationale Supérieure de Chimie de Rennes, France and Université de Genève, Switzerland
Enantioselective 1,6-Conjugate Addition of Dialkylzinc Reagents to Acyclic Dienones Catalyzed by Cu-DiPPAM Complex–Extension to Asymmetric Sequential 1,6/1,4-Conjugate Addition.
Chem. Eur. J. 2013;
19: 13663-13667
Enantioselective 1,6-Conjugate Addition of Dialkylzinc Reagents to Acyclic Dienones Catalyzed by Cu-DiPPAM Complex–Extension to Asymmetric Sequential 1,6/1,4-Conjugate Addition.
Chem. Eur. J. 2013;
19: 13663-13667
Further Information
Publication History
Publication Date:
13 December 2013 (online)
Significance
The authors reported the asymmetric 1,6-conjugate addition of dialkylzinc to acyclic dienones catalyzed by copper/phosphinoazomethinylate salt (DiPPAM). After the isomerization of the conjugate adducts, stereoselective sequential 1,4-conjugate addition of diethylzinc was also demonstrated.
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Comment
The control of regioselectivity of the 1,6-conjugate addition is difficult due to many parameters. Using copper and the DiPPAM ligand, a highly enantio- and regioselective 1,6-conjugate addition was achieved. With the BINAP ligand, unprecedented highly stereoselective induction is noteworthy.
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