Chiral Calcium Phosphate-Catalyzed Transfer Hydrogenation of β-Trifluoromethylated Nitroalkenes

Keywords

transfer hydrogenation - chiral calcium phosphate - nitroalkenes

Significance

Uchikura et al. present an asymmetric transfer hydrogenation of nitroolefins via chiral calcium phosphate catalysis in the presence of catalytic amounts of Na₃PO₄. The β-trifluoromethylated nitroalkane substrates are reduced utilizing a Hantzsch ester as a hydrogen source with 40­–97 % yield and up to 98 % ee. Notably, the system tolerates a broad range of substrates, including aryl, alkyl and heteroaryl groups, and is compatible with various perfluoroalkyl substrates.

 

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Comment

The study expands the utility of asymmetric metal phosphate catalysis and provides a new route to valuable fluorinated chiral building blocks. Notably, Terada’s early reports – initially interpreted as Brønsted acid catalysis – were later shown by Ishihara to involve metal salt catalysis. This issue was further emphasized by the List group (see Synlett 2010, 2189). Against this background, the use of a well-defined chiral calcium phosphate in the present study is both conceptually and practically significant. It establishes a clear benchmark for future work on enantioselective transfer hydrogenation using structurally defined metal phosphates in the presence of Na₃PO₄ salt as a buffer.

 

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Publikationsverlauf

Artikel online veröffentlicht:
27. August 2025