Abstract
An enantioselective organocatalyzed Henry reaction was reported using chiral ammonium aryloxides as Bronsted base organocatalysts. A wide range of aliphatic and aromatic aldehydes along with several nitroalkanes are tolerated providing the corresponding enantioenriched β-nitroalcohols with moderate to high diastereomeric ratios and up to 83 % ee. An inversion of the diastereoselectivity was observed when changing from aromatic to aliphatic aldehydes. Transition state models were proposed in order to account for this phenomenon.
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