CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines

Chang, Meng‐Yang; Lin, Chih Kuang; Pai, Chun-Li

doi:10.1016/j.tetlet.2006.02.039

Cited by 14 publications

(5 citation statements)

References 52 publications

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“…Following a similar allylation procedure for the synthesis of 14a , 220 mg (0.50 mmol, 35%) of 14b was prepared as a clear, colorless oil …”

Section: Methodsmentioning

confidence: 99%

“…Following a similar allylation procedure for the synthesis of 14a, 220 mg (0.50 mmol, 35%) of 14b was prepared as a clear, colorless oil. 103 1 H NMR (400 MHz, CDCl 3 ) δ 7.94 (d,J = 7.2 Hz,2 H),7.21 (d,J = 8.4 Hz,2 H),7.60 (t,J = 7.6 Hz,1 H),7.49 (t,J = 6.4 Hz,2 H),7.32 (d,J = 8 Hz,2 H),5.75 (m,2 H),3.86 (comp,4 H),3.51 (t,J = 4.4 Hz,2 H),3.38 (t,J = 3.2 Hz,2 H),2.46 (s,3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 198.5, 143.8, 136.6, 136.5, 133.7, 130.7, 130.4, 130.1, 128.9, 128.3, 127.4, 50.8, 43.9, 39.3, 31.5 21.8;IR (neat) 3062, 2922IR (neat) 3062, , 1681IR (neat) 3062, , 1449IR (neat) 3062, , 1339IR (neat) 3062, , 1209IR (neat) 3062, , 1156 16a). To a slurry of NaH (17 mg, 0.42 mmol) in THF (2 mL, 0.2 M) at 0 °C was added slowly dimethyl 2-(2-oxo-2-phenylethyl)malonate (100 mg, 0.4 mmol) before warming to room temperature.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics

et al. 2012

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The study presented herein describes a reductive transmetalation approach toward the generation of Grignard and organozinc reagents mediated by a titanocene catalyst. This method enables the metalation of functionalized substrates without loss of functional group compatibility. Allyl zinc reagents and allyl, vinyl, and alkyl Grignard reagents were generated in situ and used in the addition to carbonyl substrates to provide the corresponding carbinols in yields up to 99%. It was discovered that phosphine ligands effectively accelerate the reductive transmetalation event to enable the metalation of C-X bonds at temperatures as low as -40 °C. Performing the reactions in the presence of chiral diamines and amino alcohols led to the enantioselective allylation of aldehydes.

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“…Following a similar allylation procedure for the synthesis of 14a , 220 mg (0.50 mmol, 35%) of 14b was prepared as a clear, colorless oil …”

Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics

et al. 2012

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“…N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpro pylamine hydrochloride / Fluoxetine hydrochloride (1·HCl) (Chang et al 2006). -Chloroethyl chloroformate (108 µL, 1.0 mmol) was added dropwise to a solution of 3-dimethylamino-1phenyl-1-(4-trifluoromethylphenoxy)propane (5) (81 mg, 0.25 mmol) in dichloroethane (2.5 mL) at RT under argon atmosphere, in a 10 mL MW glass tube.…”

Section: 341mentioning

confidence: 99%

Ball mill and microwave assisted synthetic routes to Fluoxetine

Solà

Sutcliffe

Banks

et al. 2017

Sustainable Chemistry and Pharmacy

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“…The MBH adducts formation of N-alkyl isatins with methyl acrylate and DABCO (1,4-diazabicyclo[2.2.2]octane) in methanol afforded the desired MBH adducts (28)(29)(30)(31)(32)(33)(34)(35) in excellent yield. Accordingly, N-alkylation of isatin was carried out with CaH 2 and alkyl halide in DMF at 60 8C to afford N-alkyl isatins in excellent yield.…”

Section: Nc-h Activation Study Of Secondary Methylene Radical Sourcesmentioning

confidence: 99%

Activation of the NC–H bond of Morita–Baylis–Hillman adducts of N-substituted isatins with cerium ammonium nitrate (CAN) and alcohol (ROH)

Shanmugam

Vaithiyanathan

2009

Can. J. Chem.

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A study on the activation of the NC-H bond of Morita-Baylis-Hillman adducts of N-substituted isatin with cerium ammonium nitrate (CAN) and saturated and unsaturated alcohols have been carried out. The choice of a Morita-Baylis-Hillman adduct for this study is screened with a number of adducts. A comparative and reactivity pattern study on NC-H activation of Morita-Baylis-Hillman adducts of N-substituted isatin derivatives viz. N-methyl, N-ethyl, N-methyl acetate, N-benzyl, N-propargyl, and N-isopropyl isatins have been carried out. Effect of aryl ring substitution has also been investigated. A plausible mechanism for the formation of the ether products has been outlined.

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CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines

Cited by 14 publications

References 52 publications

Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics

Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics

Ball mill and microwave assisted synthetic routes to Fluoxetine

Activation of the NC–H bond of Morita–Baylis–Hillman adducts of N-substituted isatins with cerium ammonium nitrate (CAN) and alcohol (ROH)

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