An approach to 2-cyanopyrrolidines bearing a chiral auxiliary
Tetrahedron: Asymmetry , 2007, 18 (2), 290-297
DOI: 10.1016/j.tetasy.2007.01.008
The reaction of 2-methyl-2-((1-phenylethyl)amino)propanenitrile with different γ-halocarbonyl compounds is investigated. The influence of different parameters such as the nature of the substrate and solvent, is discussed. The reaction is considered as a convenient route to 2-cyanopyrrolidines in the case of aliphatic γ-halocarbonyl compounds possessing a reasonably reactive carbonyl group. In many cases, the products can be obtained as single enantiomers. It is shown that cyclopropyl ketones can also react with 2-methyl-2-((1-phenylethyl)amino)propanenitrile to give 2-cyanopyrrolidines. A mechanistic scheme is proposed in order to explain the experimental facts observed.
Grygorenko O. O.; Kopylova N. A.; Mikhailiuk P. K.; Meißner A.; Komarov I. V.
Tetrahedron: Asymmetry 2007, 18 (2), 290-297
DOI: 10.1016/j.tetasy.2007.01.008