Trans‐Selective Radical Silylzincation of Ynamides

作者: Elise Romain , Carolin Fopp , Fabrice Chemla , Franck Ferreira , Olivier Jackowski

DOI: 10.1002/ANIE.201407002

关键词: StereochemistrySelectivityChemistryBond formationElectrophilic additionElectrophilic substitutionPhotochemistry

摘要: The silylzincation of terminal ynamides is achieved through a radical-chain process involving (Me3Si)3SiH and R2Zn. A potentially competing polar mechanism excluded on the basis diagnostic control experiments. unique feature this addition across CC bond its trans selectivity. One-pot electrophilic substitution C sp 2Zn by CuI-mediated formation subsequent manipulation C sp 2Si provides modular access to Z-α,β-disubstituted enamides.

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