Synfacts 2011(10): 1133-1133  
DOI: 10.1055/s-0030-1261116
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Phosphoric Acid Catalyzed Transfer Hydrogenation of Ketimines

Contributor(s): Benjamin List, Anna Lee
A. Henseler, M. Kato, K. Mori, T. Akiyama*
Gakushuin University, Tokyo, Japan
Further Information

Publication History

Publication Date:
20 September 2011 (online)


Akiyama and co-workers report an asymmetric phosphoric acid catalyzed synthesis of aromatic and heteroaromatic trifluorometh­ylated amines. To show the utility of this reaction, the authors carried out the synthesis of a perfluoroalkylated analogue of the bioactive compound NPS R-568. Benzothiazoline was used as a hydride source, and it shows stronger reactivity compared to the Hantzsch ester, which is commonly used as a transfer hydrogenation agent. Also, by employing a deuterated benzothiazoline in the reaction, the authors were able to enantioselectively incorporate deuterium into the products and at the same time provide support for a hydride mechanism in the transfer hydrogenation of ketimines with benzothiazoline.