Concepedia

A Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Nitrones to Allyl Alcohol

Xia Ding, Katsumi Taniguchi, Yutaka Ukaji, Katsuhiko Inomata

Chemistry Letters · 2001 · 24 citations · 10 references

DOI

Concepts

Abstract

Abstract A highly diastereo- and enantioselective 1,3-dipolar cycloaddition of nitrones bearing an amide moiety to allyl alcohol has been realized by using a catalytic amount of diisopropyl (R,R)-tartrate as a chiral auxiliary. Addition of amine N-oxide such as pyridine N-oxide, was crucial to realize a reproducible excellent enantioselectivity up to 98% ee.

References

10

New Strategies for Organic Catalysis:  The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition

Wendy S. Jen, John J. M. Wiener, David W. C. MacMillan · Journal of the American Chemical Society · 2000 · 507 citations

, , +7

Catalytic Enantioselective 1,3-Dipolar Cycloadditions between Nitrones and Alkenes Using a Novel Heterochiral Ytterbium(III) Catalyst

Shū Kobayashi, Mikako Kawamura · Journal of the American Chemical Society · 1998 · 141 citations

, , +8

Catalytic Enantioselective Inverse-Electron Demand 1,3-Dipolar Cycloaddition Reactions of Nitrones with Alkenes

Klaus B. Simonsen, Pau Bayón, Rita G. Hazell et al. · Journal of the American Chemical Society · 1999 · 137 citations

, , +10

Highly Endo- and Enantioselective Asymmetric Nitrone Cycloadditions Catalyzed by the Aqua Complex of 4,6-Dibenzofurandiyl-2,2‘-bis(4-phenyl- oxazoline)−Nickel(II) Perchlorate. Transition Structure Based on Dramatic Effect of MS 4A on Selectivities

Shuji Kanemasa, Yoji Oderaotoshi, Junji Tanaka et al. · Journal of the American Chemical Society · 1998 · 123 citations

, , +8

Copper(II)-Bisoxazoline Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions of Nitrones with Electron-Rich Alkenes

Kim B. Jensen, Rita G. Hazell, Karl Anker Jørgensen · The Journal of Organic Chemistry · 1999 · 103 citations

, , +15