Stereoselective Reactions with Stabilized Carbocations
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.
Record created on 2011-02-06, modified on 2016-08-09