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.

作者: Akemi Ryoda , Nana Yajima , Toyokazu Haga , Takuya Kumamoto , Waka Nakanishi

DOI: 10.1021/JO701923Z

关键词: ImidazolidineImineEthyl acrylateEnantioselective synthesisBenzilDiamineChemistryMichael reactionAmmonium acetatePolymer chemistryOrganic chemistry

摘要: (±)-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 1,3-dimethyl-4,5-bis(2-methylphenyl)imidazolidine related 1,3-dibenzyl-4,5-diphenylimidazolidine examined in asymmetric Michael reaction t-butyl diphenyliminoacetate ethyl acrylate.

参考文章(10)
Mutasem Omar Sinnokrot, C. David Sherrill, High-Accuracy Quantum Mechanical Studies of π−π Interactions in Benzene Dimers Journal of Physical Chemistry A. ,vol. 110, pp. 10656- 10668 ,(2006) , 10.1021/JP0610416
Eietsu Hasegawa, Dennis P. Curran, Additive and solvent effects on samarium diiodide reductions: the effects of water and DMPU Journal of Organic Chemistry. ,vol. 58, pp. 5008- 5010 ,(1993) , 10.1021/JO00070A046
Yukari Kitani, Takuya Kumamoto, Toshio Isobe, Keiko Fukuda, Tsutomu Ishikawa, Guanidine-Catalyzed Asymmetric Trimethylsilylcyanation of Carbonyl Compounds Advanced Synthesis & Catalysis. ,vol. 347, pp. 1653- 1658 ,(2005) , 10.1002/ADSC.200505161
Francesco Babudri, Vito Fiandanese, Giuseppe Marchese, Angela Punzi, A direct access to α-diones from oxalyl chloride Tetrahedron Letters. ,vol. 36, pp. 7305- 7308 ,(1995) , 10.1016/0040-4039(95)01471-S
R. P. Duran, V. T. Amorebieta, A. J. Colussi, Pyrolysis of acetylene: a thermal source of vinylidene Journal of the American Chemical Society. ,vol. 109, pp. 3154- 3155 ,(1987) , 10.1021/JA00244A053
Tsutomu Ishikawa, Toshio Isobe, Modified guanidines as chiral auxiliaries. Chemistry: A European Journal. ,vol. 8, pp. 552- 557 ,(2002) , 10.1002/1521-3765(20020201)8:3<552::AID-CHEM552>3.0.CO;2-T
Patricia L. Watson, Robert G. Bergman, Reactivity of alkyne tungsten and molybdenum complexes. Heterolytic carbon-hydrogen bond activation in coordinated alkynes Journal of the American Chemical Society. ,vol. 102, pp. 2698- 2703 ,(1980) , 10.1021/JA00528A030
A. Kalivretenos, J. K. Stille, L. S. Hegedus, Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone Journal of Organic Chemistry. ,vol. 56, pp. 2883- 2894 ,(1991) , 10.1021/JO00008A053