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Asymmetric Nitroaldol Reaction Catalyzed by a C2-Symmetric Bisoxazolidine Ligand

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journal contribution
posted on 01.05.2008, 00:00 by Shuanglong Liu, Christian Wolf
A C2-symmetric bisoxazolidine was found to effectively catalyze the asymmetric Henry reaction of aliphatic and aromatic aldehydes. β-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.