32090-48-5Relevant academic research and scientific papers
Photosensitive Tetramethylpiperidine Urethanes: Synthesis and Characterization
Martina, Stefano,MacDonald, Scott A.,Enkelmann, Volker
, p. 3281 - 3283 (1994)
The problem of synthesizing photosensitive urethanes of the highly sterically hindered 2,2,6,6-tetramethylpiperidine is solved by first preparing the 1-chlorocarbonyl derivative which was shown to react with a series of o-nitrobenzylic alcohols, including 2,6-dinitrobenzyl alcohol.These products are potential photogenerators of this amine.Full characterization is reported, along with a crystal structure.
Formal and improved synthesis of enantiopure chiral methanol
Schweifer, Anna,Hammerschmidt, Friedrich
, p. 7605 - 7610 (2008/12/20)
[D2]Methanol was converted to the carbamate derived from 2,2,6,6-tetramethylpiperidine. It was metalated with s-BuLi/TMEDA at -78 °C with a high primary kinetic isotope effect to give an α-oxymethyllithium, which was silylated with chlorodimethylphenylsilane. The silylmethyl carbamate formed was lithiated and borylated with the borate derived from tert-butanol and (R,R)-1,2-dicyclohexylethane-1,2-diol to give diastereomeric boronates, which were separated by preparative HPLC and can in principle be converted to enantiopure chiral methanols. Thus, both enantiomers are easily accessible in nine linear steps.
