The Use of Bis(trimethylsilyl)acetamide and Bis (trimethylsilyl)urea for Protection and as Control Reagents in Synthesis

Moharem T. El Gihani; Harry Heaney

doi:10.1055/s-1998-2043

Synthesis 1998; 1998(4): 357-375
DOI: 10.1055/s-1998-2043

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The Use of Bis(trimethylsilyl)acetamide and Bis (trimethylsilyl)urea for Protection and as Control Reagents in Synthesis

Moharem T. El Gihani^* , Harry Heaney

^*Department of Chemistry, Loughborough University, Leicestershire, LE11 3TU, England; Fax + 44(0 15 09)22 39 25; E-mail: h.heaney@lboro.ac.uk

Abstract

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The oxophilicity of silicon allows the efficient protection of a range of hydroxyfunctionalities using either N,O-bis(trimethylsilyl)acetamide (BSA) or N,N-bis(trimethylsilyl)urea (BSU). Three distinct mechanistic pathways are proposed for the reactions of the reagents which explain the mild reaction conditions that can be used to achieve a number of important synthetic transformations. The reactions include examples where improved stereochemical control results from the use of BSA.

azetidinones - Friedel-Crafts reactions - Lewis acids - nitrogen heterocycles - palladium catalysis - phosphorus compounds - stereochemistry

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