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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046208
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:36:37 PM
Last modification on : Thursday, July 2, 2020 - 3:28:30 AM

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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, Wiley, 2016, 1 (12), pp.3184-3188. ⟨10.1002/slct.201600776⟩. ⟨hal-02046208⟩

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