An Isothiourea-Catalyzed Asymmetric [2,3]-Rearrangement of Allylic Ammonium Ylides

West, Thomas H.; Daniels, David S. B.; Slawin, Alexandra M. Z.; Smith, Andrew D.

doi:10.1021/ja500758n

Cited by 156 publications

(73 citation statements)

References 48 publications

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“…The 1 H NMR spectrum are in agreement with reported data by West et al 16 p-Methoxycinnamyl bromide (13) To a stirred solution of 12 (483 mg, 2.94 mmol) in Et 2 O (35 mL), PBr 3 (0.14 mL, 1.47 mmol) was added at 0 C. The reaction was stirred until complete by TLC analysis (30-45 min). The mixture was quenched with a saturated NaCl (40 mL) solution and extracted with Et 2 O (2 Â 30 mL).…”

Section: P-methoxycinnamyl Alcohol (12)supporting

confidence: 88%

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Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: anin vitrostudy

Burmaoğlu

Dilek

Yılmaz

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Two cinnamyl-substituted phloroglucinols, 4-p-methoxycinnamyl phloroglucinol (9) and 4,6-bis-p-methoxycinnamyl phloroglucinol (10) were synthesized. Two carbonic anhydrases, human carbonic anhydrase I and II (hCA I and II), were purified. Kinetic interactions between these isozymes with 9 and 10 were investigated. These new compounds exhibited inhibitory effects on the hCA I and II enzymes' activity in vitro. The combination of the inhibitory effects of both phloroglucinol and p-coumaric acid groups in a single compound was explored. However, relative to the inhibitory effects of the two groups separately, compounds 9 and 10 demonstrated comparable inhibitory effects. More effective inhibitors of CAs could be created by testing these compounds on other CA isozymes.

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Section: P-methoxycinnamyl Alcohol (12)supporting

confidence: 88%

“…The mixture was quenched with a saturated NaCl (40 mL) solution and extracted with Et 2 O (2 Â 30 mL). The organic phase was dried with Na 2 SO 4 and the solvent was evaporated under reduced pressure to yield p-methoxycinnamyl bromide (13) 16 …”

Section: P-methoxycinnamyl Alcohol (12)mentioning

confidence: 99%

Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: anin vitrostudy

Burmaoğlu

Dilek

Yılmaz

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…[25] In summary, we report the depolymerization of birch lignin leading to the isolation of a pure phenolic monomer 8 as the major product in a 5 wt % yield. To the best of our knowledge, this is the first time that compounds such as 8 (and 7) have been isolated as the major products in the depolymerization of lignin.…”

Section: Technologiestoproducechemicalsandfuelsfromrenewablementioning

confidence: 85%

Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β‐O‐4 Linkages in Lignin

et al. 2014

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Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two-step depolymerization process. Chemoselective catalytic oxidation of b-O-4 linkages promoted by the DDQ/tBuONO/ O 2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized b-O-4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.

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“…5 Building upon this work, we demonstrated an isothiourea-promoted 6,7 catalytic enantioselective [2,3]rearrangement of allylic ammonium ylides, leading to a range of α-amino acid derivatives 8 bearing either N,N-dimethyl or cyclic-N-alkyl substituents (Scheme 1c). 8 This process allows for the synthesis of a variety of α-amino ester derivatives and the incorporation of pharmacological relevant amine motifs such as the morpholine unit, although the preparation of free α-amino esters was not possible as suitable N-substituents amenable to facile deprotection were not incorporated.…”

Section: Graphical Abstractmentioning

confidence: 99%

Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides

2017

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Please cite this article as: West TH, Spoehrle SSM, Smith AD, Isothiourea-catalysed chemo-and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides, Tetrahedron (2017), doi: 10.1016/j.tet.2017.01.062. This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Leave this area blank for abstract info. The isothiourea-catalysed chemo-and enantioselective [2,3]-sigmatropic rearrangement of N,Ndiallyl allylic ammonium ylides is explored as a key part of a route to free functionalised α-amino esters and piperidines. The [2,3]-sigmatropic rearrangement proceeds with excellent diastereo-and enantiocontrol (>95:5 dr, up to 97% ee), with the resultant N,N-diallyl α-amino esters undergoing either mono-or bis-N-allyl deprotection. Bis-N-allyl deprotection leads to free α-amino esters, while the mono-deprotection strategy has been utilised in the synthesis of a target functionalised piperidine. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT

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An Isothiourea-Catalyzed Asymmetric [2,3]-Rearrangement of Allylic Ammonium Ylides

Cited by 156 publications

References 48 publications

Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: anin vitrostudy

Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: anin vitrostudy

Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β‐O‐4 Linkages in Lignin

Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides

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