Zincation and Magnesiation of Functionalized Silylated Cyano­hydrins Using TMP-Bases

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.

Key words

metalation - umpolung - organomagnesium reagents - organozinc­ reagents - benzylation

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