Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide iodo binaphtholates

Fabien Carrée; Richard Gil; Jacqueline Collin

doi:10.1021/ol0475360

Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide iodo binaphtholates

Org Lett. 2005 Mar 17;7(6):1023-6. doi: 10.1021/ol0475360.

Authors

Fabien Carrée¹, Richard Gil, Jacqueline Collin

Affiliation

¹ Laboratoire de Catalyse Moléculaire, UMR 8075, ICMMO, Bâtiment 420, Université Paris-Sud, 91405, Orsay, France.

PMID: 15760129
DOI: 10.1021/ol0475360

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%.