Palladium-catalyzed carbonylative couplings of vinylogous enolates: application to statin structures.
The first Pd-catalyzed carbonylative couplings of aryl and vinyl halides with vinylogous enolates are reported generating products derived from C-C bond formation exclusively at the γ-position. Good results were obtained with a dienolate derivative of acetoacetate (1,3-dioxin-4-one). These transformations occurred at room temperature and importantly with only stoichiometric carbon monoxide in a two-chamber reactor. The methodology was applied to the synthesis of two members of the statin family generating the cis-3,5-diol acid motif by a γ-selective carbonylation followed by a cis-stereoselective reduction of the 3,5-dicarbonyl acid intermediates.
Carbon Dioxide Activation Center (CADIAC), The Interdisciplinary Nanoscience Center (iNANO) and Department of Chemistry, Aarhus University , Gustav Wieds Vej 14, 8000 Aarhus, Denmark.
Ilya S
IS
Makarov
Carbon Dioxide Activation Center (CADIAC), The Interdisciplinary Nanoscience Center (iNANO) and Department of Chemistry, Aarhus University , Gustav Wieds Vej 14, 8000 Aarhus, Denmark.|Department of Chemistry, Graduate School of Science, Osaka Prefecture University , Sakai, Osaka 599-8531, Japan.
Takashi
T
Kuwahara
Carbon Dioxide Activation Center (CADIAC), The Interdisciplinary Nanoscience Center (iNANO) and Department of Chemistry, Aarhus University , Gustav Wieds Vej 14, 8000 Aarhus, Denmark.
Xavier
X
Jusseau
Department of Chemistry, Graduate School of Science, Osaka Prefecture University , Sakai, Osaka 599-8531, Japan.
Ilhyong
I
Ryu
Carbon Dioxide Activation Center (CADIAC), The Interdisciplinary Nanoscience Center (iNANO), Biological and Chemical Engineering, Department of Engineering, Aarhus University , Finlandsgade 22, 8200 Aarhus N, Denmark.
Anders T
AT
Lindhardt
Carbon Dioxide Activation Center (CADIAC), The Interdisciplinary Nanoscience Center (iNANO) and Department of Chemistry, Aarhus University , Gustav Wieds Vej 14, 8000 Aarhus, Denmark.
Troels
T
Skrydstrup