Bismuth Triflate‐Catalyzed Addition of Allylsilanes to <i>N</i>‐Alkoxycarbonylamino Sulfones: Convenient Access to 3‐Cbz‐Protected Cyclohexenylamines

Ollevier, Thierry; Li, Zhiya

doi:10.1002/adsc.200900710

Cited by 37 publications

(11 citation statements)

References 70 publications

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“…Compound 5 a 2, 7, 8b: The product was isolated as a white solid (yield 89 mg, 90 %) after purification by silica gel chromatography ( n ‐hexane/EtOAc=95:5). 1 H NMR (CDCl 3 , 500 MHz,): δ= 7.23–7.34 (m, 5 H), 5.63–5.72 (m, 1 H), 5.06–5.12 (m, 2 H), 4.87 (s, br, 1 H), 4.73 (s, br, 1 H), 2.51 (m, br, 2 H), 1.41 ppm (s, 9 H); 13 C NMR (CDCl 3 , 125 MHz): δ= 155.15, 142.33, 142.28, 133.96, 128.45, 127.09, 126.19, 118.12, 79.42, 53.93, 41.20, 28.32 ppm.…”

Section: Methodsmentioning

confidence: 99%

Phosphotungstic Acid as an Efficient Catalyst for Allylation of Isatins and N‐tert‐Butyloxycarbonylamido Sulfones Under Solvent‐Free Conditions

et al. 2014

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The present work demonstrates the use of phosphotungstic acid (H3PW12O40⋅H2O) as an efficient catalyst for the allylation of isatin derivatives as well as N‐tert‐butyloxycarbonyl (Boc)‐α‐amido sulfones with allyltributyltin as an allylating agent under solvent‐free conditions at room temperature. Excellent allylation product yields of up to 99 % for the isatins substrates and good to excellent yields of up to 98 % for the N‐Boc α‐amido sulfones were obtained. The present allylation protocol is scalable as demonstrated by allylation of N‐methylisatin at 1 g scale. Based on 1H, 13C, and 31P NMR studies a catalytic cycle was proposed for allylation of isatins as well as N‐Boc amido sulfones. The allylation products N‐Boc homoallyl amines were successfully epoxidized to get multifunctional compounds, which are valuable intermediates for natural products and bioactive compounds.

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Section: Methodsmentioning

confidence: 99%

Phosphotungstic Acid as an Efficient Catalyst for Allylation of Isatins and N‐tert‐Butyloxycarbonylamido Sulfones Under Solvent‐Free Conditions

et al. 2014

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“…A recent report of an asymmetric catalyst for the Strecker reaction is of particular interest (Scheme ) . It uses an α‐amido sulphone as starting material, and sulfone 13 could be prepared in a manner analogous to that reported for the Katritzky precursor or from by‐product 11 . This route would also necessitate the synthesis of the catalyst as well.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2 C‐14 labeled cathepsin C inhibitors: The use of a cyanide to displace a Benzotriazole

Kingston

Bergare

Lönn

et al. 2017

Labelled Comp Radiopharmac

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In support of the development of a new treatment for COPD, 2 C-14 labeled compounds were required for in vitro animal studies. The synthesis of nitrile [ C]-1 was completed in 3 steps from C-14 labeled 4-bromobenzonitrile in accord with the previously developed medicinal chemistry route. The second compound, 2, did not possess an arylnitrile as did 1, which made the synthetic design more complex. An advanced, unlabeled benzotriazole containing intermediate, 10, was synthesized in low yield over 3 steps and was subsequently reacted with K CN to give a mixture of diastereomers 12. Separation of the diastereomers followed by deprotection afforded [ C]-2 in a 13% radiochemical yield.

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“…Bi(OTf ) 3 has been disclosed by our group to be an efficient catalyst in the Sakurai reaction of allyltrimethylsilanes with N-alkoxycarbonylamino sulfones. 46 The reaction proceeded smoothly with a low catalyst loading of Bi(OTf ) 3 (2-5 mol%) to afford the corresponding protected homoallylic amines in very good yields (up to 96%) (Scheme 40, eqn (1)). The generality of our method was further extended to a functionalized allylsilane.…”

Section: N-alkoxycarbonylamino Sulfone Allylation Reactionsmentioning

confidence: 99%

New trends in bismuth-catalyzed synthetic transformations

Ollevier

2013

Org. Biomol. Chem.

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206

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This review covers uses of bismuth catalysts since 2005 with a special emphasis on the emerging applications of such catalysts. Low toxicity, low catalytic loading, synergistic effects with other catalysts, and some hydrocompatibility properties confer to bismuth salts major advantages. The expanding activity in the field clearly highlights the growing potential of bismuth catalysts. The article is not a comprehensive review on bismuth catalysis but a selection of its most promising uses in challenging synthetic transformations.

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Bismuth Triflate‐Catalyzed Addition of Allylsilanes to N‐Alkoxycarbonylamino Sulfones: Convenient Access to 3‐Cbz‐Protected Cyclohexenylamines

Cited by 37 publications

References 70 publications

Phosphotungstic Acid as an Efficient Catalyst for Allylation of Isatins and N‐tert‐Butyloxycarbonylamido Sulfones Under Solvent‐Free Conditions

Phosphotungstic Acid as an Efficient Catalyst for Allylation of Isatins and N‐tert‐Butyloxycarbonylamido Sulfones Under Solvent‐Free Conditions

Synthesis of 2 C‐14 labeled cathepsin C inhibitors: The use of a cyanide to displace a Benzotriazole

New trends in bismuth-catalyzed synthetic transformations

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