Tandem Brook Rearrangement/Silicon Polonovski Reaction via Oxidative Generation of Ammonium Ylides

Hiromasa Shibuya; Takahiro Nakago; Seiichi Inoue; Yujiro Hoshino; Kiyoshi Honda

doi:10.5650/jos.ess16022

Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics (TEAC)

Tandem Brook Rearrangement/Silicon Polonovski Reaction via Oxidative Generation of Ammonium Ylides

Hiromasa Shibuya, Takahiro Nakago, Seiichi Inoue, Yujiro Hoshino, Kiyoshi Honda

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Keywords: tertiary amine N-oxides, Polonovski reaction, Brook rearrangement, tandem reaction, dealkylation

JOURNAL FREE ACCESS

2017 Volume 66 Issue 8 Pages 833-842

DOI https://doi.org/10.5650/jos.ess16022

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Abstract

A tandem Brook rearrangement/silicon Polonovski reaction has been achieved by in situ generation of ammonium ylides via the oxidation of α-silyl-tertiary amines. Furthermore, we found that the oxidation of N-(1-cyano-1-silyl)methyl-tertiary amines with peracids induced the tandem Brook rearrangement/silicon Polonovski reaction/fragmentation to give formamide derivatives in moderate yields.

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