155397-14-1Relevant academic research and scientific papers
1,1-Disilyl alcohols as d1 synthons: Harnessing the 1,2-Brook rearrangement
Fleming, Ian,Lawrence, Annabel J.,Richardson, Robert D.,Surry, David S.,West, Mark C.
, p. 3349 - 3365 (2007/10/03)
1,1-Disilyl alcohols like 6 give the silyl ethers like 9 on treatment with base and alkyl halides, in a reaction which may be formulated as the alkylation of the Brook-rearranged carbanion 8. The products can be oxidised to give ketones like 10, showing that this Brook-rearranging system supplies a controlled d1 synthon of the acyl anion class. The alcohols can be prepared from the acid chloride 12 and dimethyl(phenyl)silyllithium, but the intermediate anion 21 need not be worked up; it can be used directly in the alkylation step.
Synthesis of Acylsilanes from Amides and Esters, and the Selective Oxidation of α-Silyl Alcohols to Aldehydes
Fleming, Ian,Ghosh, Usha
, p. 257 - 262 (2007/10/02)
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 phenyldimethylsilyllithium followed by oxidation of the disilyl alcohols 5 with PDC.The disilyl alcohols 5 can be used as intermediates in the conversion of esters into aldehydes without recourse to hydride reagents, by monodesilylation, using a Brook rearrangement, followed by oxidation and selective removal of the silyl group, using chromium trioxide in DMSO.
