Chiral Ammonium Aryloxides as Brønsted Base Catalysts for the Henry Reaction of Nitroalkanes to Aromatic and Aliphatic Aldehydes

Jérémy Godemert (1) , Sylvain Oudeyer (1) , Vincent Levacher (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

An enantioselective organocatalyzed Henry reaction was reported using chiral ammonium aryloxides as Brønsted 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.

Domaines: Chimie

Jérémy Godemert, Sylvain Oudeyer, Vincent Levacher. Chiral Ammonium Aryloxides as Brønsted Base Catalysts for the Henry Reaction of Nitroalkanes to Aromatic and Aliphatic Aldehydes. ChemistrySelect, 2016, 1 (12), pp.3184-3188. ⟨10.1002/slct.201600776⟩. ⟨hal-02046208⟩