Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles

JacsStereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles: Allylboronic esters react readily with carbonyls and imines ( π-electrophiles), but are unreactive toward a range of other electrophiles. By addition of an aryllithium, the corresponding allylboronate complexes display enhanced nucleophilicity, enabling addition to a range of electrophiles (tropylium, benzodithiolylium, activated pyridines, Eschenmoser’ s salt, Togni’s reagent, Selectfluor, diisopropyl azodicarboxylate (DIAD), MeSX) in high regio- and stereocontrol. This protocol provides access to key new functionalities, including quaternary stereogenic centers bearing moieties such as fluorine and the trifluoromethyl group.

Source: Organometallic Current - October 25, 2017 Category: Chemistry Tags: Allylic Source Type: blogs