Switch in stereoselectivity caused by the isocyanide structure in the rhodium-catalyzed silylimination of alkynes.

J Am Chem Soc

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

Published: July 2011

The reaction of terminal alkynes with hydrosilanes and tert-alkyl isocyanides in the presence of Rh(4)(CO)(12) gives (Z)-β-silyl-α,β-unsaturated imines in good yields. On the other hand, the use of aryl isocyanides in place of tert-alkyl isocyanides leads to the formation of E isomers.

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http://dx.doi.org/10.1021/ja202881yDOI Listing

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