Lithiation of a Silyl Ether: Anionic Si→C Alkyl Migration

Abstract

This article describes a new synthetic utility of silyl ethers, the lithiation of which leads to an alkyl group migration from the silyl ether to the carbonyl group of the amide in the ortho position, forming a ketone. Additionally, the combination of the well-established anionic Fries rearrangement of lithiated carbamates to give hydroxyamides is discussed herein.

Key words

alkylation - hydroxyketone - rearrangement - α-silyl carbanions - synthetic methods

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