The disodium salt of (4
R,5
R)-(TADDOL), 3, can be used as a mediator in the asymmetric Michael reaction,
e.g. 1,4-addition of a glycine synthon 1 to methyl methacrylate 2, mediated by 3 (10–100 ...mol%), gives a diastereoisomeric excess of the corresponding product 4 up to 65% and an enantiomeric purity
ca. 28%; (2
S,4
R)-4-methylglutamic acid (ee ≥ 85%), 6, was obtained starting from (2
S,4
R)-4 (ee 28%) through the recrystallization and decomposition of the latter.
