Aminal–Pyrrolidine Organocatalysts – Highly Efficient and Modular Catalysts for alpha-Functionalization of Carbonyl Compounds

The substitution of the 4-position of hydroxyproline by aphenol group, together with an aminal on the 2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the alpha-functionalization of a wide range of linear/branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and alpha-amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to 1000 h–1 could be obtained.

Références

Titre
Aminal–Pyrrolidine Organocatalysts – Highly Efficient and Modular Catalysts for alpha-Functionalization of Carbonyl Compounds
Type de publication
Article de revue
Année de publication
2010
Revue
European Journal of Organic Chemistry
Volume
2010
Ticket
5
Pagination
927–936
Soumis le 7 septembre 2022