Hyperconjugative effect of C-Ge bonds: synthesis of multisubstituted alkenylgermanes via torquoselective olefination of acylgermanes with ynolates

Mitsuru Shindo, Kenji Matsumoto, Kozo Shishido

Research output: Contribution to journalArticle

16 Citations (Scopus)

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 languageEnglish
Pages (from-to)4271-4277
Number of pages7
JournalTetrahedron
Volume63
Issue number20
DOIs
Publication statusPublished - May 14 2007

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Decarboxylation
Protonation
Lactones
Acids

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 journalArticle

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