Yu. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, S. A. Orlova, V. V. Smirnov, A. A. Chesnokov, “Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate”, Mendeleev Commun., 1997, Volume 7, Issue 4,Pages <nobr>137

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Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate

Yu. N. Belokon^a, K. A. Kochetkov^a, T. D. Churkina^a, N. S. Ikonnikov^a, S. A. Orlova^a, V. V. Smirnov^b, A. A. Chesnokov^b

^a A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
^b Higher Chemical College of the Russian Academy of Sciences, D.I. Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation

Abstract: The disodium salt of (4R,5R)-(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%; (2S,4R)-4-methylglutamic acid (ee ≥ 85%), 6, was obtained starting from (2S,4R)-4 (ee 28%) through the recrystallization and decomposition of the latter.

Language: English

DOI: 10.1070/MC1997v007n04ABEH000790