Chiral phosphoric acid catalyzed redox deracemization of triarylmethanes

Abstract

Described here is the first deracemization of triaryl-substituted carbon stereocenters, which is in contrast to the well-established processes to deracemize monoaryl- and diaryl-substituted ones. This one-pot redox process involves in situ generation of a para-quinone methide intermediate followed by asymmetric reduction by chiral phosphoric acid catalysis. A wide range of highly enantioenriched triarylmethanes could be generated with high efficiency under mild conditions.

Keywords

Triarylmethanes / deracemization / para-quinone methide / chiral phosphoric acid

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