Concepedia

Design of a New and Highly Effective Chiral Auxiliary for Diels−Alder Reaction of 1-Aminodiene

Raphaël Robiette, Karima Cheboub‐Benchaba, Daniel Peeters, J. Marchand‐Brynaert

The Journal of Organic Chemistry · 2003 · 42 citations · 5 references

DOIFull text

Open access

Concepts

Abstract

A theoretical investigation of the facial selectivity of optically active oxazolidin-2-one-substituted dienes has been realized. This analysis enabled the development of (R)-4-phenyloxazolidin-2-thione as a very effective chiral auxiliary for cycloaddition of 1-aminodiene.

References

5

New Strategies for Organic Catalysis:  The First Highly Enantioselective Organocatalytic Diels−Alder Reaction

Kateri A. Ahrendt, Christopher J. Borths, David W. C. MacMillan · Journal of the American Chemical Society · 2000 · 1.7K citations

, , +9

Asymmetric olefin epoxidation with sodium hypochlorite catalyzed by easily prepared chiral manganese(III) salen complexes

Wei Zhang, Eric N. Jacobsen · The Journal of Organic Chemistry · 1991 · 480 citations

, , +8

Kinetics and mechanism of oxidation of aromatic hydrocarbons by Ru(trpy)(bpy)O2+

Mark S. Thompson, Thomas J. Meyer · Journal of the American Chemical Society · 1982 · 170 citations

, , +11

Asymmetric Diels-Alder reaction catalyzed by chiral bases

Olivier Riant, Henri B. Kagan · Tetrahedron Letters · 1989 · 78 citations

, , +10

Nucleophilic additions to phosphine oxides. A model study of anionic trigonal bipyramidal intermediates

Carol A. Deakyne, Leland C. Allen · Journal of the American Chemical Society · 1976 · 10 citations

, , +6