Fe(OTf) 3 -catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones

Tao, Ruiheng; Yin, Yan; Duan, Yongbin; Sun, Yuxing; Sun, Yue; Cheng, Fengkai; Pan, Jinpeng; Cheng, Lu; Wang, Yuan

doi:10.1016/j.tet.2017.02.030

Cited by 22 publications

(9 citation statements)

References 39 publications

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“…This transformation did not occur with tertiarty propargylic alcohols. Finally, this method was employed for the preparation of the drug Fluoxetine, in racemic form [60] …”

Section: Cascade Reactions Starting By a Meyer Schuster Rearrangementmentioning

confidence: 99%

“…Finally, this method was employed for the preparation of the drug Fluoxetine, in racemic form. [60] Oxygen-based nucleophiles also performed 1,4-additions after MSR (Scheme 19). Propargylic alcohols reacted with Bi (OTf) 3 15 at 5 mol% to give the intermediate enones, which were trapped by various types of alcohols, affording the ethers 78.…”

Section: Msrs Followed By Intermolecular 14 Additionsmentioning

confidence: 99%

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Recent Developments in the Meyer‐Schuster Rearrangement

Justaud¹,

Hachem

Grée³

2021

Eur J Org Chem

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Most of this review article has been prepared during Covid 19 pandemy. Therefore, we dedicate it,-first to all persons who unfortunately died from this disease and,-second to all people (medical doctors and many others) who helped their congeners to survive to this pandemy. The Meyer-Schuster rearrangement is an efficient method to prepare α,β-unsatured carbonyl compounds starting from propargylic alcohols and this review presents the remarkable progress made during the last decade in this reaction. New efficient catalytic systems have been discovered and many elegant applications have been reported for this rearrangement. To be noticed in particular are the new and efficient cascade processes affording a wide range of carbo-and heterocyclic molecules. Moreover, brilliant applications of this rearrangement have been described as well, in the total synthesis of complex natural products and their analogues. Finally, the first examples of aza-Meyer-Schuster rearrangements have been recently described as well.

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“…This transformation did not occur with tertiarty propargylic alcohols. Finally, this method was employed for the preparation of the drug Fluoxetine, in racemic form [60] …”

Section: Cascade Reactions Starting By a Meyer Schuster Rearrangementmentioning

confidence: 99%

Section: Msrs Followed By Intermolecular 14 Additionsmentioning

confidence: 99%

Recent Developments in the Meyer‐Schuster Rearrangement

Justaud¹,

Hachem

Grée³

2021

Eur J Org Chem

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“…Previous studies also indicated that only primary 3‐aryl propargyl alcohols underwent the transformation smoothly and led to β‐amino ketones in high yields. Propargyl alcohols with bulky group α to −OH, and 3‐phenylprop‐2‐yn‐1‐ols with 4‐NO 2 or 4‐CN were not tolerated for this trasformation of β‐amino ketones [11b] . So, a series of primary 3‐aryl propargyl alcohols 1 a – 1 o were prepared through a Pd 2+ ‐catalyzed Sonogashira coupling reaction of Ar−X and commercial available prop‐2‐yn‐1‐ol (Scheme 3), [11,12] and the scope was explored for the one‐pot synthesis of α‐bromo‐β‐amino ketones from propargyl alcohols 1 with TsNH 2 as the nucleophile and NBS as the halogen source (Table 4).…”

Section: Resultsmentioning

confidence: 98%

“…Our previous studies on the acid‐catalyzed reaction of propargyl alcohols and nitrogen nucleophilis indicated that nucleophilicity of nitrogen nucleophilis had dominant effect on the reaction, and only sulfonamides were well tolerated and afforded the corresponding β‐amino ketones in high yields [11b] . So, the effec of sulfonamides on the transformation of 1a to α‐bromo‐β‐amino ketones was then invesigated, and the resutls indicated that all sulfonamides underwent this reaction smoothly and led to corresponding α‐bromo‐β‐amino ketones in 51–92% yields (Table 3).…”

Section: Resultsmentioning

confidence: 99%

Bi(OTf)₃‐catalyed One‐pot Synthesis of α‐Halo‐β‐amino Ketones and Acyl Aziridines from 3‐Aryl Propargyl Alcohols

Duan

Guo

Yang

et al. 2021

Chemistry An Asian Journal

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A Bi(OTf)3‐catalyed reaction of 3‐aryl propargyl alcohols with sulfonamide and halogen source was firstly investigated, which provided a facile route for the synthesis of a large variety of α‐halo‐β‐amino ketones. The key intermediates, β‐amino ketones, were obtained through tandem Meyer‐Schuster rearrangement reaction of propargyl alcohols and intermolecular Michael addition of α, β‐unsaturated ketones and sulfonamide. Then the in situ generated α‐halo‐β‐amino ketones underwent the base‐promoted intramolecular cyclization to give diverse acyl aziridines in a one‐pot fashion. These transformations are reliable on a large scale. The high yields and convenient experimental operations make it a valuable method for the construction of α‐halo‐β‐amino ketones and acyl aziridine derivatives.

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“…-Amino ketones also exhibit a number of biological activities, including antiinflammatory, anticancer, antituberculosis, antibacterial, analgesic, antitussive, and other drug activities. 7 In addition, they can be easily converted into ,-unsaturated ketones, 1,3-amino alcohols, or other functional ketones. -Amino ketones have been synthesized by conventional Mannich reactions of aldehydes, ketones, and amines.…”

mentioning

confidence: 99%

Acid-Mediated Denitrogenation/Rearrangement/Coupling of Benzyl Azides with Triazolyl-Substituted Cycloalkanones

Che¹,

Wang

Fu³

et al. 2020

Synlett

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Organic molecules containing α-triazolyl or β-amino cyclic ketone fragments have been individually proven to show good bioactivities and to be useful in asymmetric and pharmaceutical syntheses. A triflic acid-promoted simple and efficient method for the synthesis of unsymmetrical α-triazolyl-α′-(aminomethyl)cycloalkanones from benzyl azides and α-triazolylcycloalkanones has been developed. A series of unsymmetrical α,α′-disubstituted cycloalkanones were obtained with high syn-diastereoselectivity and up to 82% yield. Examination of the reaction mechanism showed that the benzyl azides undergo protonation, nitrogen elimination, rearrangement, and electrophilic attack by the enol forms of the cyclic ketones.

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Fe(OTf) 3 -catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones

Cited by 22 publications

References 39 publications

Recent Developments in the Meyer‐Schuster Rearrangement

Recent Developments in the Meyer‐Schuster Rearrangement

Bi(OTf)₃‐catalyed One‐pot Synthesis of α‐Halo‐β‐amino Ketones and Acyl Aziridines from 3‐Aryl Propargyl Alcohols

Acid-Mediated Denitrogenation/Rearrangement/Coupling of Benzyl Azides with Triazolyl-Substituted Cycloalkanones

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Fe(OTf) 3 -catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones

Cited by 22 publications

References 39 publications

Recent Developments in the Meyer‐Schuster Rearrangement

Recent Developments in the Meyer‐Schuster Rearrangement

Bi(OTf)3‐catalyed One‐pot Synthesis of α‐Halo‐β‐amino Ketones and Acyl Aziridines from 3‐Aryl Propargyl Alcohols

Acid-Mediated Denitrogenation/Rearrangement/Coupling of ­Benzyl Azides with Triazolyl-Substituted Cycloalkanones

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Product

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Bi(OTf)₃‐catalyed One‐pot Synthesis of α‐Halo‐β‐amino Ketones and Acyl Aziridines from 3‐Aryl Propargyl Alcohols

Acid-Mediated Denitrogenation/Rearrangement/Coupling of Benzyl Azides with Triazolyl-Substituted Cycloalkanones