TY - JOUR
T1 - Palladium-Catalyzed Carbonylative Couplings of Vinylogous Enolates
T2 - Application to Statin Structures
AU - Makarov, Ilya S.
AU - Kuwahara, Takashi
AU - Jusseau, Xavier
AU - Ryu, Ilhyong
AU - Lindhardt, Anders T.
AU - Skrydstrup, Troels
PY - 2015/11/11
Y1 - 2015/11/11
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84947461203&partnerID=8YFLogxK
U2 - 10.1021/jacs.5b09342
DO - 10.1021/jacs.5b09342
M3 - Article
AN - SCOPUS:84947461203
VL - 137
SP - 14043
EP - 14046
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 44
ER -