Synlett 2014; 25(20): 2827-2830
DOI: 10.1055/s-0034-1379493
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© Georg Thieme Verlag Stuttgart · New York

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

Chin-Yin Lin
Institute of Chemistry, Academia Sinica, 128 Academia Road Sec. 2, Nankang Taipei 11529, Taiwan   Fax: +886(2)27831237   Email: rjchein@chem.sinica.edu.tw
,
Rong-Jie Chein*
Institute of Chemistry, Academia Sinica, 128 Academia Road Sec. 2, Nankang Taipei 11529, Taiwan   Fax: +886(2)27831237   Email: rjchein@chem.sinica.edu.tw
› Author Affiliations
Further Information

Publication History

Received: 10 September 2014

Accepted after revision: 17 October 2014

Publication Date:
18 November 2014 (online)

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.

 
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