Tetrahedron p. 2473 - 2482 (1990)
Update date:2022-08-02
Topics: Regioselectivity Diastereoselectivity Column chromatography Yield NMR spectroscopy Steric hindrance Enantiomeric excess (ee) Dipolarophile Nitrile oxide HPLC (high-performance liquid chromatography) Intramolecular Reaction Solvent Effects Catalyst Loading Transition state stabilization Chiral Auxiliary Temperature Control Lewis Acid Catalysis 1,3-Dipolar Cycloaddition Nitrone Intermolecular reaction
Olsson, Thomas
Stern, Kaye
Westman, Gunnar
Sundell, Staffan
With simple chiral esters, cycloaddition reactions are performed in high yields with considerable diastereoselectivities. Evidence for the preferred conformation of the enoates in the transition state of the nitrile oxide addition is provided and the stereoselectivity of nitrone additions is discussed.
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