Organocatalytic Asymmetric α-Selenenylation of Aldehydes

摘要

Asymmetric organocatalysis has become a field of central importance for the stereoselective preparation of chiral, enantioenriched molecules.[1] In particular, chiral secondary amine catalysis has proven to be a powerful procedure for the enantioselective transformation of carbonyl compounds. Aminocatalysis has enabled the asymmetric α-, β-, and γ-functionalization of aldehydes and ketones with a wide range of electrophiles and nucleophiles by exploiting catalytic enamine,[2] SOMO (singly occupied molecular orbital),[3] iminium ion,[4] and dienamine[5] activation modes (Scheme 1). Within the realm of the non-inert elements classified as non-metals in the periodic table, only selenium-based compounds have yet to be stereoselectively incorporated into carbonyl compounds by organocatalysis.[6]