80424-18-6Relevant articles and documents
Chiral Bis(imidazolidine)iodobenzene (I-Bidine) Organocatalyst for Thiochromane Synthesis Using an Asymmetric Michael/Henry Reaction
Arai, Takayoshi,Suzuki, Takumi,Inoue, Takahiro,Kuwano, Satoru
supporting information, p. 122 - 127 (2016/12/26)
Bis(imidazolidine)iodobenzene (I-Bidine) was designed as an organocatalyst based on previously reported imidazolidine- or oxazolidine-containing chiral metal catalysts. I-Bidine showed catalytic activity for the Michael/Henry reaction of thiosalicyl aldeh
A practical solvating agent for the chiral NMR discrimination of carboxylic acids
Kim, Seon-Mi,Choi, Kihang
experimental part, p. 4747 - 4750 (2011/10/09)
A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and (S,S)-1,2-diphenylethylenediamine through a single-step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates
One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates
Fujioka, Hiromichi,Murai, Kenichi,Kubo, Ozora,Ohba, Yusuke,Kita, Yasuyuki
, p. 638 - 643 (2007/10/03)
Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphatic aldehydes and N-nonsubstituted and N-monosubstituted 1,2-diamines. Furthermore, it was found that CH2Cl2 could be altered to TBME, a more environmentally friendly solvent, in the reaction using N-nonsubstituted 1,2-diamines. The reaction conditions were very mild and chemoselective.
Organocatalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated enones using novel imidazoline catalysts
Halland, Nis,Hazell, Rita G.,Jorgensen, Karl Anker
, p. 8331 - 8338 (2007/10/03)
A new catalytic enantioselective conjugate addition of nitroalkanes to acyclic α,β-unsaturated enones catalyzed by novel organic catalysts has been developed. A series of chiral amines has been tested as catalysts for the addition of 2-nitropropane to benzylideneacetone, and it is found that a novel imidazoline catalyst, prepared from phenylalanine, can catalyze a highly enantioselective 1,4addition reaction. The reaction of various acyclic and cyclic nitroalkanes was found to proceed well with enantioselectivities up to 86% ee, and enantiopure products can be obtained by recrystallization. The potential of the reaction is documented by the reaction of a series of substituted α,β-unsaturated enones with different nitroalkanes. Furthermore, the synthetic applicability of the reaction is demonstrated by the formation of optically active functionalized pyrrolines and pyrrolidines by reductive amination of the products. On the basis of the absolute configuration of the conjugate addition products, the mechanism for the reaction is discussed and a transition state proposed.
A simplified synthesis of (±)-1,2-Diphenyl-1,2-diaminoethane (1) from benzaldehyde and ammonia. Revision of the structures of the long-known intermediates 'hydrobenzamide' and 'amarine'
Corey,Kuehnle, Florian N. M.
, p. 8631 - 8634 (2007/10/03)
A new pathway for the simple, stereocontrolled and economical synthesis of (±)-1 from benzaldehyde is described. The structures of two intermediates (Scheme 1) have been revised to those shown in Scheme 2.
