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J Org Chem. 2008 Jan 4;73(1):133-41. Epub 2007 Dec 7.

Optical resolution of (+/-)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine as a chiral framework for 2-iminoimidazolidine with 2-methylphenyl pendant and the guanidine-catalyzed asymmetric michael reaction of tert-butyl diphenyliminoacetate and ethyl acrylate.

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  • 1Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.

Abstract

(+/-)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine, prepared from benzil and ammonium acetate, was optically resolved as a chiral framework for 2-(1-benzyl-2-hydroxyethyl)imino-1,3-dimethylimidazolidine with 2-methylphenyl pendants at the 4,5-positions. Catalysis ability of the 1,3-dimethyl-4,5-bis(2-methylphenyl)imidazolidine and the related 1,3-dibenzyl-4,5-diphenylimidazolidine was examined in the asymmetric Michael reaction of t-butyl diphenyliminoacetate and ethyl acrylate.

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