3,3'-Diiodobinaphthol and 3,3'-Diiodobiphenol Derivatives as Hypervalent Iodine Organocatalysts for the α-Oxytosylation of Ketones.

New series of enantiopure 3,3'-diiodobinaphthol I (R = Ac, 2-phenylpropanol, 4-tolylformamide, N-isopropylformamide, etc.) and 3,3'-diiodobiphenol-based mols. e.g., II have been synthesized and used as chiral hypervalent iodine oxidn. organocatalysts in the alpha-oxytosylation of propiophenone. These new organocatalysts were compared to previous series of 3,3'-diiodo-1,1'-binaphthalene-2,2'-diol-fused maleimides, two important observations have made: the maleimide moiety is the best moiety for obtaining moderate enantioselectivities, and the presence of an aliph. substituent on the biaryl part of the catalyst enhances the enantioselectivity.

Références

Titre
3,3'-Diiodobinaphthol and 3,3'-Diiodobiphenol Derivatives as Hypervalent Iodine Organocatalysts for the α-Oxytosylation of Ketones.
Type de publication
Article de revue
Année de publication
2015
Revue
Synthesis
Volume
47
Pagination
3859–3873
ISSN
1437-210X
Soumis le 12 avril 2018