I. Fleming et U. Ghosh, SYNTHESIS OF ACYLSILANES FROM AMIDES AND ESTERS, AND THE SELECTIVE OXIDATION OF ALPHA-SILYL ALCOHOLS TO ALDEHYDES, Journal of the Chemical Society. Perkin transactions. I, (3), 1994, pp. 257-262
The acylsilanes 2 can easily be made directly from the dimethylamides
3 by treatment with phenyldimethylsilyllithium. They can also be made
in two steps from the esters 4 using 2 equiv. of phenyldimethylsilylli
thium followed by oxidation of the disilyl alcohols 5 with PDC. The di
silyl alcohols 5 can be used as intermediates in the conversion of est
ers into aldehydes without recourse to hydride reagents, by monodesily
lation, using a Brook rearrangement. followed by oxidation and selecti
ve removal of the silyl group, using chromium trioxide in DMSO.