Benzylic carbocations, which are easily generated in situ from alcohols or acetates by Brønsted or Lewis acids, undergo selective facial discrimination in diastereoselective reactions (see scheme; FG=functional group). The A values are responsible for the facial selectivity. Catalytic amounts of various Lewis acids can be employed in discriminating one face of the carbocation.
Shubhajit Das, Rubén Laplaza Solanas, Jacob Terence Blaskovits
Simone Gallarati, Raimon Fabregat I De Aguilar-Amat, Veronika Juraskova, Théo Pierre Jaffrelot Inizan