Mt. Elgihani et H. Heaney, THE USE OF BIS(TRIMETHYLSILYL) ACETAMIDE AND BIS(TRIMETHYLSILYL) UREAFOR PROTECTION AND AS CONTROL REAGENTS IN SYNTHESIS, Synthesis, (4), 1998, pp. 357-375
The oxophilicity of silicon allows the efficient protection of a range
of hydroxyfunctionalities using either N,O-bis(trimethylsilyl)acetami
de (BSA) or N,N-bis(trimethylsilyl)urea (BSU). Three distinct mechanis
tic pathways are proposed for the reactions of the reagents which expl
ain 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.