Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines to Homoallylic Alcohols

Katsuyoshi Tanaka, Tomomitsu Kato, Shuhei Fujinami, Yutaka Ukaji, Katsuhiko Inomata

Chemistry Letters · 2010 · 36 citations · 20 references

Concepts

Abstract

Abstract The asymmetric 1,3-dipolar cycloaddition of azomethine imines to homoallylic alcohols was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to give the corresponding optically active trans-pyrazolidines with excellent regio-, diastereo-, and enantioselectivities. The catalytic use of diisopropyl (R,R)-tartrate was also effective in the presence of MgBr2.

References

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