Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide iodo binaphtholates |
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Authors: | Carrée Fabien Gil Richard Collin Jacqueline |
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Institution: | Laboratoire de Catalyse Moléculaire, UMR 8075, ICMMO, Batiment 420, Université Paris-Sud, 91405, Orsay, France. |
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Abstract: | reaction: see text] Lanthanide iodo binaphtholates are efficient enantioselective catalysts for the ring opening of meso-epoxides by various aromatic amines. The study of the influence of temperature on the ring opening of cyclohexene oxide by o-anisidine catalyzed by the samarium complex shows an isoinversion effect with the maximum enantiomeric excess at -40 degrees C. Reactions of aniline, o-anisidine, or p-anisidine with five- or six-membered ring epoxides at this temperature allow the preparation of beta-amino alcohols with enantiomeric excesses up to 93%. |
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