2006
DOI: 10.1021/jo052510n
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Supramolecular Catalysis of Strecker Reaction in Water under Neutral Conditions in the Presence of β-Cyclodextrin

Abstract: An environmentally benign and highly efficient procedure for the nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction) has been developed under biomimetic conditions in water in the presence of beta-cyclodextrin to afford alpha-aminonitriles in quantitative yields. The use of cyclodextrin precludes the use of either acid or base, and the catalyst can be recycled a number of times without loss in activity.

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Cited by 95 publications
(45 citation statements)
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“…It has been reported that the Strecker reaction of acetophenone even with the activated amine 3,4,5-trimethylaniline using metal triflates and acetonitrile as the solvent gave very poor yield of the product (47)(48)(49). We found that a similar reaction of acetophenone with aniline and TMSCN (cyanide source) in dichloromethane using Ga(OTf) 3 as a catalyst proceeds smoothly under mild conditions (room temperature, 5 h) giving the corresponding ␣-aminonitrile in excellent yield and high purity ( Table 2, entry 1), despite that the direct Strecker reaction using aromatic ketones and aromatic amines has been repeatedly cited in the literature as a challenge (6,7,(37)(38)(39)(40)(41)(42)(43)(44)(45)(46). We performed the reaction with a variety of ketones and anilines at room temperature in dichloromethane, and in all cases high yields of the nitrile products were obtained emphasizing the generality of our methodology.…”
Section: Resultsmentioning
confidence: 69%
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“…It has been reported that the Strecker reaction of acetophenone even with the activated amine 3,4,5-trimethylaniline using metal triflates and acetonitrile as the solvent gave very poor yield of the product (47)(48)(49). We found that a similar reaction of acetophenone with aniline and TMSCN (cyanide source) in dichloromethane using Ga(OTf) 3 as a catalyst proceeds smoothly under mild conditions (room temperature, 5 h) giving the corresponding ␣-aminonitrile in excellent yield and high purity ( Table 2, entry 1), despite that the direct Strecker reaction using aromatic ketones and aromatic amines has been repeatedly cited in the literature as a challenge (6,7,(37)(38)(39)(40)(41)(42)(43)(44)(45)(46). We performed the reaction with a variety of ketones and anilines at room temperature in dichloromethane, and in all cases high yields of the nitrile products were obtained emphasizing the generality of our methodology.…”
Section: Resultsmentioning
confidence: 69%
“…In summary, the application of Ga(OTf) 3 as an effective water tolerable, reusable catalyst for the Strecker reaction has been demonstrated. Our studies show that not only aldehydes but also ketones and f luorinated ketones can efficiently undergo the Strecker reaction under very mild conditions using Ga(OTf) 3 as the catalyst in dichloromethane. Various metal trif lates show good catalytic activity for the Strecker reaction.…”
Section: Resultsmentioning
confidence: 96%
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