3 years ago
Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles
Kathryn Feeney, Christopher Sandford, Varinder K. Aggarwal, Jack L.-Y. Chen, Herbert Mayr, Guillaume Berionni, Paula Lorenzo, Cristina García-Ruiz
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. The allylboronate complexes were determined to be 7 to 10 orders of magnitude more reactive than the parent boronic ester.
Publisher URL: http://dx.doi.org/10.1021/jacs.7b10240
DOI: 10.1021/jacs.7b10240
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