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Regio- and Stereoselective N-addition to an Open Bromo Vinyl Cation

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Abstract A protocol for the synthesis of thus far inaccessible bromo vinyl triflimides is presented. Our previously reported concept of assisted vinyl cation formation was engaged to achieve both a… Click to show full abstract

Abstract A protocol for the synthesis of thus far inaccessible bromo vinyl triflimides is presented. Our previously reported concept of assisted vinyl cation formation was engaged to achieve both a protonation of relatively electron poor bromo alkynes and a reaction with high regio- and stereoselectivity. To the best of our knowledge, this is the first stereoselective addition of an N-nucleophile to an open β-halovinyl cation.

Keywords: cation; vinyl cation; stereoselective addition; bromo vinyl; bromo

Journal Title: Tetrahedron Letters
Year Published: 2021

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