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Synlett 1991; 1991(3): 160-162
DOI: 10.1055/s-1991-20662
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2-Trimethylsiloxy-1,3-dioxolanes: A Novel Protective Group for Carboxylic Acids

Delia Waldmüller* , Manfred Braun, Alois Steigel
  • *Institut für Organische Chemie und Makromolekulare Chemie der Universität Düsseldorf, Universitätsstraße 1, D-4000 Düsseldorf 1, Germany
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Publication Date:
07 March 2002 (online)

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Carboxylic acids 1 are protected effectively as silyl ortho esters 2 (2-alkyl-2-trimethylsiloxy-4,4,5-triphenyl-1,3-dioxolanes) by esterification with triphenylglycol, deprotonation with butyllithium or lithium diisopropylamide and subsequent treatment with chlorotrimethylsilane. The novel protective group, which can be introduced and removed under non-acidic conditions, displays stability against alkyllithium reagents.