Catalytic Asymmetric Addition Reactions of Formaldehyde ,-Dialkylhydrazone to Synthesize Chiral Nitrile Derivatives.

Réactions d'addition asymétrique catalytique de la formaldéhyde ,-dialkylhydrazone pour la synthèse de dérivés nitriles chiraux.

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ID: 108595
2020
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Abstract
A number of nitrile-containing chiral molecules were synthesized via asymmetric nucleophilic addition of formaldehyde ,-dialkylhydrazone as the nitrile equivalent. Chiral '-dioxide/metal salt complexes enabled the asymmetric addition reactions to both isatin-derived imines and α,β-unsaturated ketones, generating amino nitriles and 4-oxobutanenitrile derivatives in good yields with high enantioselectivities. This protocol was highlighted by avoiding the use of toxic nitrile reagents, wide substrate scope, and versatile transformations of chiral hydrazone adducts into other valuable molecules.
Une série de molécules chirales contenant un groupe nitrile a été synthétisée par addition nucléophile asymétrique de la ,-dialkylhydrazone de formaldéhyde en tant qu'équivalent de nitrile. Des complexes chiraux de '-dioxyde/sel métallique ont permis les réactions d'addition asymétrique tant sur des imines dérivées de l'isatine que sur des cétones α,β-insaturées, générant des aminonitriles et des dérivés de 4-oxobutanenitrile avec de bons rendements et des énantiosélectivités élevées. Ce protocole se distingue par l'absence d'utilisation de réactifs nitriles toxiques, un large champ de substrats et des transformations polyvalentes des adduits d'hydrazone chiraux en d'autres molécules à haute valeur ajoutée.
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zhang2020catalyticorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Zhang, Hang;Luo, Yao;Zhu, Chenhao;Dong, Shunxi;Liu, Xiaohua;Feng, Xiaoming;
Journal Organic letters
Year 2020
DOI
10.1021/acs.orglett.0c01857
URL
Keywords
hydroxyapatite dental caries polymeric micelles farnesal ph-sensitive

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