Abstract
Alkali metal salts of substituted (S)-prolines, alkali metal alkoxides of (S)-prolinol, and Na salts of chiral substituted 2-amino-2"-hydroxy-1,1"-binaphthyls can catalyze the asymmetric Michael reaction of diethyl malonate with crotonaldehyde to give adducts in >90% yields with ee up to 40%. The influences of the catalyst structure, the nature of the alkali metal cation, temperature, the solvent, and salt additives on the reaction outcome were studied.
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Kochetkov, K.A., Harutyunyan, S.R., Kuz"mina, N.A. et al. Asymmetric Michael reaction of diethyl malonate with crotonaldehyde catalyzed by chiral aminocarboxylates, amino alcoholates, and amino phenolates. Russian Chemical Bulletin 50, 1620–1624 (2001). https://doi.org/10.1023/A:1013090619703
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DOI: https://doi.org/10.1023/A:1013090619703