Elsevier

Tetrahedron

Volume 53, Issue 38, 22 September 1997, Pages 13139-13148
Tetrahedron

New one-pot method for the stereoselective synthesis of (E)-[β-(trifluoromethylsulfonyloxy)-alkenyl](Aryl) iodonium triflates

https://doi.org/10.1016/S0040-4020(97)00836-3Get rights and content

Abstract

The reactions of reagent 1 with acetylenes leading to the alkenyl(aryl)iodonium triflates have been investigated. The results indicate that the very simple and efficient one-pot conversion of terminal alkynes into alkenyl(aryl)iodonium triflates described in this paper presents several advantages over the previously described procedure. The stereoselectivity of these reactions is discussed on the basis of physico-chemical evidence including IR, NMR spectroscopy and X-ray analysis. It is shown that these reactions are accompanied with anti-addition to afford (E)-[β-(trifyloxy)alkenyl](aryl) iodonium triflates in moderate to excellent yields. A possible mechanism is also discussed.

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