Trans-selective radical silylzincation of ynamides

Autor: Elise Romain, Fabrice Chemla, Martin Oestreich, Franck Ferreira, Carolin Fopp, Alejandro Perez-Luna, Olivier Jackowski
Rok vydání: 2014
Předmět:
Zdroj: Angewandte Chemie (International ed. in English). 53(42)
ISSN: 1521-3773
Popis: The silylzincation of terminal ynamides is achieved through a radical-chain process involving (Me3Si)3SiH and R2Zn. A potentially competing polar mechanism is excluded on the basis of diagnostic control experiments. The unique feature of this addition across the C≡C bond is its trans selectivity. One-pot electrophilic substitution of the C(sp2)-Zn bond by Cu(I)-mediated C-C bond formation and subsequent manipulation of the C(sp2)-Si bond provides a modular access to Z-α,β-disubstituted enamides.
Databáze: OpenAIRE