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Synfacts 2009(7): 0759-0759
DOI: 10.1055/s-0029-1217279
DOI: 10.1055/s-0029-1217279
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Diastereoselective Acid-Catalyzed Ritter Reaction
P. Rubenbauer, T. Bach*
Technische Universität München, Garching, Germany
Further Information
Publication History
Publication Date:
22 June 2009 (online)
Significance
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.