131180-55-7Relevant academic research and scientific papers
Fluorinated organocatalysts for the enantioselective epoxidation of enals: Molecular preorganisation by the fluorine-iminium ion Gauche effect
Tanzer, Eva-Maria,Zimmer, Lucie E.,Schweizer, W. Bernd,Gilmour, Ryan
supporting information, p. 11334 - 11342,9 (2020/08/31)
The fluorine-iminium ion gauche effect is triggered upon union of a secondary β-fluoroamine and an α,β-unsaturated aldehyde, providing a useful strategy for controlling the molecular topology of intermediates that are central to organocatalytic processes. The β-fluoroamine (S)-2-(fluorodiphenylmethyl)pyrrolidine (1) is an effective catalyst for the enantioselective epoxidation of α,β-unsaturated aldehydes. A process of structural editing has revealed that the efficiency of this catalyst is due to the (fluorodiphenyl)methyl group when it is embedded in a β-fluoroiminium motif. Epoxidations of challenging cyclic α,β-disubstituted, β,β-disubstituted and α,β,β-trisubstituted enals catalysed by 1 proceed with excellent levels of enantiocontrol (up to 98 % ee). Fluorine finesse. The β-fluoroamine (S)-2-(fluorodiphenylmethyl)pyrrolidine (1) is an effective catalyst for the enantioselective epoxidation of α,β-unsaturated aldehydes (see scheme). Application of this catalyst to challenging cyclic α,β-disubstituted enals, β,β-disubstituted enals, and an α,β,β-trisubstituted enal proceeds in a highly enantioselective fashion (up to 98 % ee). Copyright
A Practical Enantioselective Synthesis of α,α-Diaryl-2-pyrrolidinemethanol. Preparation and Chemistry of the Corresponding Oxazaborolidines
Mathre, David J.,Jones, Todd K.,Xavier, Lyndon C.,Blacklock, Thomas J.,Reamer, Robert A.,et al.
, p. 751 - 762 (2007/10/02)
A practical two-step enantioselective synthesis of α,α-diaryl-2-pyrrolidinemethanols (1) from proline, based on the addition of aryl Grignard reagents to proline-N-carboxanhydride (3), is reported.An investigation into the chemistry of the corresponding B-alkyl- and B-aryloxazaborolidines (2) led to the development of a reliable procedure for their preparation.
