Asymmetric Nitroaldol Reaction Catalyzed by a C2-Symmetric Bisoxazolidine Ligand

A C2-symmetric bisoxazolidine was found to effectively catalyze the asymmetric Henry reaction of aliphatic and aromatic aldehydes. Beta-hydroxy nitroalkanes were produced in up to 99% yield and 95% ee. The bisoxazolidine-catalyzed nitroaldol formation requires relatively short reaction times, proceeds under mild conditions and is applicable to a wide range of substrates including sterically hindered aldehydes.