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Synfacts 2015; 11(1): 0079
DOI: 10.1055/s-0034-1379647
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Trans-Selective Silylzincation of Terminal Ynamides

Contributor(s):
Paul Knochel
,
Diana Haas
Romain E, Fopp C, Chemla F, Ferreira F, Jackowski O, Oestreich M, * Perez-Luna A. * Université Pierre et Marie Curie, Paris, France and Technical University of Berlin, Germany
Trans-Selective Radical Silylzincation of Ynamides.

Angew. Chem. Int. Ed. 2014;
53: 11333-11337
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

zinc - copper - silylation

Significance

The authors report a regio- and ­stereoselective silylzincation reaction of terminal ynamides using (Me3Si)3SiH and diethyl zinc. The resulting vinylzinc intermediates are trapped by a copper(I)-mediated substitution reaction to obtain Z-β-silylenamides in high yields.


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Comment

The radical-chain process involves an addition of the (Me3Si)3Si radical to the ynamide to provide a Z-configured α-amino vinylic radical which reacts with the dialkylzinc reagent by ­homolytic substitution to afford a α-zincated β-silylenamide.


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