2021
DOI: 10.1002/ejoc.202100090
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Remarkable Effect of tert‐Amine Additives in the Asymmetric Direct Michael Reaction of Ketones with β‐Arylnitroethenes Catalyzed by an L‐Hydroxyproline‐Based Amino Tf‐Amide Organocatalyst

Abstract: A catalytic asymmetric direct Michael reaction of ketones with trans-β-arylnitroethenes can be achieved under the influence of optically pure L-hydroxyproline-based secondary-amino aromatic Tf-amide organocatalyst. The effect of the trialkylamine base additive such as diethylmethylamine is of paramount importance to accomplish high reactivity and enantioselectivity in this asymmetric Michael reaction.

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Cited by 5 publications
(6 citation statements)
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“…In addition to developing new efficient catalysts, the identification of suitable additives has sometimes provided great improvement in catalytic performance . Brønsted bases have been used as additives in several organocatalytic asymmetric reactions, where they mainly assist proton transfer, act as acid scavengers, or transform a less-efficient catalyst into a highly performing one. …”
Section: Introductionmentioning
confidence: 99%
“…In addition to developing new efficient catalysts, the identification of suitable additives has sometimes provided great improvement in catalytic performance . Brønsted bases have been used as additives in several organocatalytic asymmetric reactions, where they mainly assist proton transfer, act as acid scavengers, or transform a less-efficient catalyst into a highly performing one. …”
Section: Introductionmentioning
confidence: 99%
“…The catalyst XV showed intriguing result in asymmetric Michael reaction. When the reaction between cyclohexanone ( 39 a ) and trans ‐ β ‐nitrostyrene ( 64 a ) was carried out in the presence of 10 mol% of XV , no reaction was observed for 48 hours, disappointingly (Scheme 38a, entry 1) [38] . This result is ascribed to the zwitterion formation between acidic Tf‐amide and basic secondary‐amine.…”
Section: Modified Chiral Amino Aromatic Tf‐amide Catalysismentioning
confidence: 99%
“…Treatment of cyclohexanones and nitrostyrenes in the presence of benzoic acid and organocatalyst is a standard protocol of these researches (Scheme 13). [41][42][43][44] Chen's [41] group applied pyrrolidinyl-sulfamide catalyst 20 for this benchmark reaction. By choosing n-Hexane and dichloromethane using as cosolvent, excellent catalytic performance was observed whether eletron-withdrawing or donating group substituted on the aromatic ring of the nitroolefins.…”
Section: Nitroolefinsmentioning
confidence: 99%
“…In a recent study of sulfonamide catalyzed Michael reactions of ketones to nitroolefins, novel L ‐hydroxyproline‐based sulfonamide 21 was prepared for organocatalytic synthesis by Maruoka [44] and coworkers (Scheme 13). Unlike most studies in which 10–20 mol% of benzoic acid was necessary for the process, 1 equivalent of trialkylamine was added into system instead of acid additive for enhancing the nucleophilic character of 21 .…”
Section: Catalyst Application: Michael Additionmentioning
confidence: 99%