Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides.

@article{Longmire2002HighlyEA,
  title={Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides.},
  author={James M. Longmire and Bin Wang and Xumu Zhang},
  journal={Journal of the American Chemical Society},
  year={2002},
  volume={124 45},
  pages={
          13400-1
        }
}
A highly reactive Ag(I)-catalyzed [3 + 2] cycloaddition of azomethine ylides is founded using AgOAc as the catalytic precursor and phosphines as ligands. Using a new bis-ferrocenyl amide phosphine (FAP) as the ligand, we found that high enantioselectivities (up to 97% ee) have been achieved in the [3 + 2] cycloaddition of azomethine ylides. Up to four stereogenic centers can be established in this multicomponent coupling reaction from readily available materials such as aldehydes, aminoesters… 

Figures and Tables from this paper

A new trifluoromethylated sulfonamide phosphine ligand for Ag(i)-catalyzed enantioselective [3 + 2] cycloaddition of azomethine ylides.

A newly developed Ming-Phos ligand with a 3,5-bis(trifluoromethyl)phenyl substituent was demonstrated to be highly efficient for Ag-catalyzed asymmetric [3 + 2] cycloaddition reactions of azomethine

Cu(I)-catalyzed highly exo-selective and enantioselective [3 + 2] cycloaddition of azomethine ylides with acrylates.

A novel Cu(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with acrylates has been developed and up to 98% enantiomeric excess have been achieved.

Bifunctional AgOAc-catalyzed asymmetric [3 + 2] cycloaddition of azomethine ylides.

A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands, providing an efficient and convenient route to optically active pyrrolidine derivatives.

Catalytic Asymmetric [3+3] Cycloaddition of Azomethine Ylides with C3‐Substituted 2‐Indolylmethanols

The first catalytic asymmetric [3+3] cycloaddition of azomethine ylides with C3-substituted 2-indolylmethanols has been established, leading to diastereo- and enantioselective construction of a

Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones.

A general protocol for the enantioselective catalytic 1,3-dipolar cycloaddition of azomethine ylides with aryl vinyl sulfones is described and the resulting enantioenriched 3-sulfonyl cycloadducts are versatile intermediates in the synthesis of 2,5-disubstituted pyrrolidines.

β-Silyl Acrylates in Asymmetric [3 + 2] Cycloadditions Affording Pyrrolidine Azasugar Derivatives.

A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with 3-silyl unsaturated esters with potential biological activities by the reduction of two ester groups and carbon-silicon bond oxidation is developed.

Diastereo- and Enantioselective Copper(I)-Catalyzed Intermolecular [3+2] Cycloaddition of Azomethine Ylides with β-Trifluoromethyl β,β-Disubstituted Enones.

This method provides scalable and efficient access to the highly substituted pyrrolidines with a trifluoromethylated, all-carbon quaternary stereocenter in good yields with up to greater than 20:1 d.r. and 98 % ee.

Cu(I)-Catalyzed asymmetric exo-selective synthesis of substituted pyrrolidines via a 1,3-dipolar cycloaddition reaction.

An (R)-DM-BINAP/Cu(CH3CN)4BF4 complex catalyzed exo-selective asymmetric 1,3-dipolar cycloaddition of imino esters with α,β-unsaturated pyrazoleamides with excellent enantioselectivities has been developed.
...

Highly Enantioselective Ag(I)-Catalyzed [3 + 2] Cycloaddition of Azomethine Ylides

  • 2002