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.
(+/-)-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.
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Akemi
A
Ryoda
Nana
N
Yajima
Toyokazu
T
Haga
Takuya
T
Kumamoto
Waka
W
Nakanishi
Masatoshi
M
Kawahata
Kentaro
K
Yamaguchi
Tsutomu
T
Ishikawa
D000085:Acetates / Q000737:chemistry*; D000179:Acrylates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D005029:Ethylenediamines / Q000138:chemical synthesis* / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry*; D048289:Imidazolidines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
C527312:1,2-bis(2-methylphenyl)ethylene-1,2-diamine; C527313:2-(1-benzyl-2-hydroxyethyl)imino-1,3-dimethylimidazolidine; D000085:Acetates; D000179:Acrylates; D005029:Ethylenediamines; D048289:Imidazolidines; D007097:Imines; C508278:tert-butyl diphenyliminoacetate; C040833:ethyl acrylate; D019791:Guanidine