Synthesis
DOI: 10.1055/s-0036-1590887
paper
© Georg Thieme Verlag Stuttgart · New York

Zincation and Magnesiation of Functionalized Silylated Cyano­hydrins Using TMP-Bases

Alicia Castelló-Micó, Paul Knochel*
  • Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
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Publication History

Received: 21 July 2017

Accepted after revision: 27 July 2017

Publication Date:
24 August 2017 (eFirst)

Abstract

Polyfunctional silylated cyanohydrins are readily magnesiated or zincated with TMPMgCl·LiCl or TMP2Zn·2MgCl2·2LiCl leading to the corresponding metallated derivatives. These Mg- or Zn-derivatives react with various electrophiles such as benzylic bromides, allylic bromides, acid chlorides, aldehydes, NCCO2Et, or MeSO2SMe. Subsequently, TBAF-deprotection provides the corresponding keto or 1,2-diketo derivatives.

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