1262525-50-7Relevant academic research and scientific papers
Evaluating the use of chiral anthracene templates to access pyroglutamic acids
Hasbullah, Siti Aishah,Jones, Simon
, p. 2719 - 2725 (2010)
An approach for the asymmetric synthesis of pyroglutamic acid derivatives is described based on an anthracene chiral auxiliary. The introduction of a furan ring as a masked carboxylic acid moiety proceeded with excellent levels of diastereo-selectivity, followed by conversion into a carboxylate ester. The ensuing retro-Diels-Alder procedure using flash vacuum pyrolysis (FVP) followed by reduction gave pyroglutamate esters in good yield but poor enantioselectivity, the latter of which was found to be dependant on the electronic nature of the N-protecting group.
