Synfacts 2009(7): 0759-0759  
DOI: 10.1055/s-0029-1217279
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Acid-Catalyzed Ritter Reaction

Contributor(s): Mark Lautens, Praew Thansandote
P. Rubenbauer, T. Bach*
Technische Universität München, Garching, Germany
Further Information

Publication History

Publication Date:
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.