A New, Simple, and Selective Palladium-Catalyzed Cleavage of Triethylsilyl Ethers

Abstract

[reaction: see text] A simple procedure for the cleavage of triethylsilyl (TES) ethers in the presence of 10 wt % Pd/C in methanol or 95% ethanol is reported. This method allows selective removal of alkyl TES ethers in the presence of aromatic TES ethers or tert-butyldimethylsilyl (TBS) protecting groups.

Illicium Sesquiterpenes: Divergent Synthetic Strategy and Neurotrophic Activity Studies

“…It should be noted that under higher pressure of H 2 (>110 bar) the hydrogenation was mildly accelerated but we observed concomitant desilylation of the C-7 triethylsilyl ether. [40] The last functionalization at the C-10 center was inspired by Danishefsky's synthesis of jiadifenin. [20] 〈-Hydroxylation with the Davis oxaziridine [41] produced 〈-hydroxy lactone 33 (stereochemistry not assigned).…”

C–H-Functionalization logic guides the synthesis of a carbacyclopamine analog

“…The hydrogenation of the so-obtained diene 4 (for its structure see Scheme 1) proceeded smoothly (H 2 , cat. Pd/C, MeOH, 25 °C, 82% yield) under concomitant removal of the triethylsilyl ether [31] in 12-position to give methyl ester 9 as a single diastereoisomer. At this point, extensive experimentation suggested a change of protecting groups to enable the pending C–H insertion reaction at C17.…”

A Divergent and Stereoselective Approach for the Syntheses of Some Polyhydroxylated Indolizidine and Pyrrolizidine Iminosugars

“…[18] The ozonolysis of the terminal olefin in 16 afforded an aldehyde. Next, we successfully carried out a one-pot stereoselective intramolecular reductive amination [20] and selective deprotection of the triethylsilyl (TES) group [21] by using 10 % Pd/ C and ammonium formate in methanol at reflux to give piperidine derivative 18. Next, we successfully carried out a one-pot stereoselective intramolecular reductive amination [20] and selective deprotection of the triethylsilyl (TES) group [21] by using 10 % Pd/ C and ammonium formate in methanol at reflux to give piperidine derivative 18.…”