55676-70-5Relevant academic research and scientific papers
Synthetic and mechanistic studies of the aza-retro-claisen rearrangement. a facile route to medium ring nitrogen heterocycles
Boeckman Jr., Robert K.,Genung, Nathan E.,Chen, Ke,Ryder, Todd R.
supporting information; experimental part, p. 1628 - 1631 (2010/06/19)
An efficient synthesis of medium-sized heterocyclic rings was achieved using a one-pot aza-Wittig/retro-aza-Claisen sequence of vinyl cyclobutanecarboxaldehydes derived from simple allylic carbonates. The use of various Staudinger reagents in the aza-Wittig reaction allows for a variety of N-substituted products to be obtained. The rearrangement is under thermodynamic control driven by relief of the cyclobutane ring strain and resonance stabilization of the resulting vinylogous amide/sulfonamide.
FLUORINE-CONTAINING AMINO ACIDS. V. IMINES OF TRIFLUOROPYRUVIC ACID IN THE SYNTHESIS OF N-SUBSTITUTED TRIFLUOROALANINES
Soloshonok, V. A.,Yagupol'skii, Yu. L.,Kukhar, V. P.
, p. 1478 - 1482 (2007/10/02)
N-Substituted trifluoroalanine methyl esters were obtained by the reduction of the corresponding imines of trifluoropyruvic acid with zinc in acetic acid.The N-butyl- and N-(1-phenylethyl)imines undergo a -proton shift under the influence of bases with the formation of trifluoroalanine derivatives.It was found that the N-(1-phenylethyl)imine of tetrafluoropyruvic acid is formed directly from the corresponding amine and methyl trifluoropyruvate under conditions with azeotropic distillation of the water with toluene in the presence of acidic catalysis.
