TY - JOUR
T1 - Hyperconjugative effect of C-Ge bonds
T2 - synthesis of multisubstituted alkenylgermanes via torquoselective olefination of acylgermanes with ynolates
AU - Shindo, Mitsuru
AU - Matsumoto, Kenji
AU - Shishido, Kozo
N1 - Funding Information:
We thank Professor S. Kanemasa (Kyushu University) for valuable discussions and Dr. J. Tanaka for X-ray crystal structure analysis. This research was supported by a Grant in Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.
PY - 2007/5/14
Y1 - 2007/5/14
N2 - The first highly Z-selective olefination of acylgermanes with ynolates affording multisubstituted alkenylgermanes was achieved. The torquoselectivity was ascribed to the hyperconjugative effect of C-Ge bonds in the transition state. The resulting (Z)-β-trialkylgermylacrylic acid has a hypervalent structure, which was converted into novel germalactones. A stereochemical complementary olefination via protonation of the β-lactone enolate, followed by decarboxylation, was also achieved.
AB - The first highly Z-selective olefination of acylgermanes with ynolates affording multisubstituted alkenylgermanes was achieved. The torquoselectivity was ascribed to the hyperconjugative effect of C-Ge bonds in the transition state. The resulting (Z)-β-trialkylgermylacrylic acid has a hypervalent structure, which was converted into novel germalactones. A stereochemical complementary olefination via protonation of the β-lactone enolate, followed by decarboxylation, was also achieved.
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U2 - 10.1016/j.tet.2007.03.048
DO - 10.1016/j.tet.2007.03.048
M3 - Article
AN - SCOPUS:34047244419
SN - 0040-4020
VL - 63
SP - 4271
EP - 4277
JO - Tetrahedron
JF - Tetrahedron
IS - 20
ER -