Concepedia

Enantio- and Diastereoselective Synthesis of Isoxazolidines by Asymmetric 1,3-Dipolar Cycloaddition of Nitrones

Yutaka Ukaji, Katsumi Taniguchi, K. Sada, Katsuhiko Inomata

Chemistry Letters · 1997 · 28 citations · 7 references

DOI

Concepts

Abstract

Abstract The asymmetric 1,3-dipolar cycloaddition of nitrones possessing electron withdrawing group to an achiral allyl alcohol was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo- and enantioselectivity.

References

7

Control of Diastereo- and Enantioselectivity in Metal-Catalyzed 1,3-Dipolar Cycloaddition Reactions of Nitrones with Alkenes. Experimental and Theoretical Investigations

Kurt V. Gothelf, Rita G. Hazell, Karl Anker Jørgensen · The Journal of Organic Chemistry · 1996 · 146 citations

, , +16

A Highly Diastereoselective and Enantioselective Ti(OTos)<sub>2</sub>−TADDOLate-Catalyzed 1,3-Dipolar Cycloaddition Reaction of Alkenes with Nitrones

Kurt V. Gothelf, Ib Thomsen, Karl Anker Jørgensen · Journal of the American Chemical Society · 1996 · 134 citations

, , +12

Dramatic solvents effects on the enantioselectivity of chiral oxazaborolidine catalyzed asymmetric 1,3-dipolar cycloadditions of nitrones with ketene acetals

Jean-Paul G. Seerden, Marcel M. M. Kuypers, Hans W. Scheeren · Tetrahedron Asymmetry · 1995 · 84 citations

, , +13

Metallic base-induced and Lewis acid-catalyzed nitrone cycloadditions to allyl alcohol dipolarophiles. Highly effective regio- and stereocontrol

Shuji Kanemasa, Takashi Tsuruoka, Eiji Wada · Tetrahedron Letters · 1993 · 58 citations

, , +8

Palladium-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones to olefins

Kazushige Hori, Hidehiko Kodama, Tetsuo Ohta et al. · Tetrahedron Letters · 1996 · 54 citations

, , +10