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Diastereoselective Acid-Catalyzed Ritter Reaction
P. Rubenbauer, T. Bach*
Technische Universität München, Garching, Germany
22 June 2009 (online)
In a rare study of carbenium ions inducing facial selectivity in SN1 reactions, an asymmetric Ritter reaction is described for chiral secondary benzylic alcohols. Using trifluoro-methanesulfonic acid, amides with high anti selectivity are produced. In contrast, the use of dinitrobenzenesulfonic acid provides syn-selective products.