Silver-Catalyzed [2 + 2] Cycloadditions of Siloxy Alkynes
2004; American Chemical Society; Volume: 126; Issue: 24 Linguagem: Inglês
10.1021/ja048251l
ISSN1943-2984
AutoresRandy F. Sweis, Michael P. Schramm, Sergey A. Kozmin,
Tópico(s)Catalytic Alkyne Reactions
ResumoWe have described the first [2 + 2] cycloadditions of siloxy alkynes with a range of unsaturated carbonyl compounds. The reactions are efficiently promoted by substoichiometric amount of silver trifluoromethanesulfonimide and display excellent regio- and diastereoselectivity combined with a broad substrate scope. Our studies have established unambiguously the stepwise mechanism of this process and provided evidence for a novel role of silver in the catalytic cycle of the reaction, which involves silver-based complexation and activation of siloxy alkyne toward the subsequent 1,4-addition.
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