Concepedia

Silver Acetate Catalysed Asymmetric1,3-Dipolar Cycloadditions of Imines and Chiral Acrylamides

Miklós Nyerges, David Bendell, Andrea Arany, David E. Hibbs, Simon J. Coles, Michael B. Hursthouse, Paul W. Groundwater, Otto Meth‐Cohn

Synlett · 2003 · 33 citations · 26 references

DOI

Concepts

Abstract

N-Metallated azomethine ylides 5 were generated by the reaction of arylidene glycine imines 1 with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides 2 with excellent diastereoselectivity. The configuration of two of the cycloadducts (3a(1) and 3c(1)) has been confirmed by Xray crystallography.

References

26

Recent advances in asymmetric synthesis using chiral lithium amide bases

Peter O’Brien · Journal of the Chemical Society Perkin Transactions 1 · 1998 · 240 citations

, , +4

The asymmetric synthesis of (-)-quinocarcin via a 1,3-dipolar cycloadditive strategy

Philip Garner, Wen Bin Ho, Hunwoo Shin · Journal of the American Chemical Society · 1993 · 81 citations

, , +8

An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

Osamu Kitagawa, Hirotaka Izawa, Takeo Taguchi et al. · Tetrahedron Letters · 1997 · 78 citations

, , +5

Asymmetric synthesis of trans-2,5-diphenylpyrrolidine: A C2-symmetric chiral amine

J. Michael Chong, Ian S. Clarke, I. Koch et al. · Tetrahedron Asymmetry · 1995 · 72 citations

, , +4

An Asymmetric Route to the Conanine BCDE Ring System. A Formal Total Synthesis of (+)-Conessine

Michael E. Kopach, Andrew H. Fray, A. I. MEYERS · Journal of the American Chemical Society · 1996 · 60 citations

, , +10