Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 4271-4277 |
| Number of pages | 7 |
| Journal | Tetrahedron |
| Volume | 63 |
| Issue number | 20 |
| DOIs | |
| Publication status | Published - May 14 2007 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Hyperconjugative effect of C-Ge bonds : synthesis of multisubstituted alkenylgermanes via torquoselective olefination of acylgermanes with ynolates. / Shindo, Mitsuru; Matsumoto, Kenji; Shishido, Kozo.
In: Tetrahedron, Vol. 63, No. 20, 14.05.2007, p. 4271-4277.Research output: Contribution to journal › Article
}
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
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.
UR - http://www.scopus.com/inward/record.url?scp=34047244419&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34047244419&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.03.048
DO - 10.1016/j.tet.2007.03.048
M3 - Article
AN - SCOPUS:34047244419
VL - 63
SP - 4271
EP - 4277
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 20
ER -