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Enantiospecific Alkynylation of Alkylboronic Esters.

Angewandte Chemie (International ed. in English)

Wang Y, Noble A, Myers EL, Aggarwal VK.
PMID: 26934427
Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4270-4. doi: 10.1002/anie.201600599. Epub 2016 Mar 02.

Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction. The process involves use of α-lithio vinyl bromide or vinyl carbamate species, for which application to Zweifel-type reactions has...

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Wang Y, Noble A, Myers EL, et al. Enantiospecific Alkynylation of Alkylboronic Esters. Angew Chem Int Ed Engl. 2016;55(13):4270-4doi: 10.1002/anie.201600599.
Wang, Y., Noble, A., Myers, E. L., & Aggarwal, V. K. (2016). Enantiospecific Alkynylation of Alkylboronic Esters. Angewandte Chemie (International ed. in English), 55(13), 4270-4. https://doi.org/10.1002/anie.201600599
Wang, Yahui, et al. "Enantiospecific Alkynylation of Alkylboronic Esters." Angewandte Chemie (International ed. in English) vol. 55,13 (2016): 4270-4. doi: https://doi.org/10.1002/anie.201600599
Wang Y, Noble A, Myers EL, Aggarwal VK. Enantiospecific Alkynylation of Alkylboronic Esters. Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4270-4. doi: 10.1002/anie.201600599. Epub 2016 Mar 02. PMID: 26934427; PMCID: PMC4804747.
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Metal vinylidenes and allenylidenes in catalysis: applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis.

Angewandte Chemie (International ed. in English)

Bruneau C, Dixneuf PH.
PMID: 16521143
Angew Chem Int Ed Engl. 2006 Mar 27;45(14):2176-203. doi: 10.1002/anie.200501391.

The involvement of a catalytic metal vinylidene species was proposed for the first time in 1986 to explain the regioselective formation of vinyl carbamates directly from terminal alkynes, carbon dioxide, and amines. Since this initial report, various metal vinylidenes...

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Bruneau C, Dixneuf PH. Metal vinylidenes and allenylidenes in catalysis: applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis. Angew Chem Int Ed Engl. 2006;45(14):2176-203doi: 10.1002/anie.200501391.
Bruneau, C., & Dixneuf, P. H. (2006). Metal vinylidenes and allenylidenes in catalysis: applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis. Angewandte Chemie (International ed. in English), 45(14), 2176-203. https://doi.org/10.1002/anie.200501391
Bruneau, Christian, and Dixneuf, Pierre H. "Metal vinylidenes and allenylidenes in catalysis: applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis." Angewandte Chemie (International ed. in English) vol. 45,14 (2006): 2176-203. doi: https://doi.org/10.1002/anie.200501391
Bruneau C, Dixneuf PH. Metal vinylidenes and allenylidenes in catalysis: applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis. Angew Chem Int Ed Engl. 2006 Mar 27;45(14):2176-203. doi: 10.1002/anie.200501391. PMID: 16521143.
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The RXR Agonist MSU42011 Is Effective for the Treatment of Preclinical HER2+ Breast Cancer and Kras-Driven Lung Cancer.

Cancers

Leal AS, Moerland JA, Zhang D, Carapellucci S, Lockwood B, Krieger-Burke T, Aleiwi B, Ellsworth E, Liby KT.
PMID: 34638488
Cancers (Basel). 2021 Oct 06;13(19). doi: 10.3390/cancers13195004.

(1) Background: Notwithstanding numerous therapeutic advances, 176,000 deaths from breast and lung cancers will occur in the United States in 2021 alone. The tumor microenvironment and its modulation by drugs have gained increasing attention and relevance, especially with the...

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Leal AS, Moerland JA, Zhang D, et al. The RXR Agonist MSU42011 Is Effective for the Treatment of Preclinical HER2+ Breast Cancer and Kras-Driven Lung Cancer. Cancers (Basel). 2021;13(19)doi: 10.3390/cancers13195004.
Leal, A. S., Moerland, J. A., Zhang, D., Carapellucci, S., Lockwood, B., Krieger-Burke, T., Aleiwi, B., Ellsworth, E., & Liby, K. T. (2021). The RXR Agonist MSU42011 Is Effective for the Treatment of Preclinical HER2+ Breast Cancer and Kras-Driven Lung Cancer. Cancers, 13(19), . https://doi.org/10.3390/cancers13195004
Leal, Ana S, et al. "The RXR Agonist MSU42011 Is Effective for the Treatment of Preclinical HER2+ Breast Cancer and Kras-Driven Lung Cancer." Cancers vol. 13,19 (2021). doi: https://doi.org/10.3390/cancers13195004
Leal AS, Moerland JA, Zhang D, Carapellucci S, Lockwood B, Krieger-Burke T, Aleiwi B, Ellsworth E, Liby KT. The RXR Agonist MSU42011 Is Effective for the Treatment of Preclinical HER2+ Breast Cancer and Kras-Driven Lung Cancer. Cancers (Basel). 2021 Oct 06;13(19). doi: 10.3390/cancers13195004. PMID: 34638488; PMCID: PMC8508021.
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Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts.

Chemical communications (Cambridge, England)

Kotozaki M, Chanthamath S, Fujii T, Shibatomi K, Iwasa S.
PMID: 29717307
Chem Commun (Camb). 2018 May 15;54(40):5110-5113. doi: 10.1039/c8cc02286k.

An asymmetric synthesis of various trifluoromethyl cyclopropanes from olefins, such as vinyl ferrocene, vinyl ethers, vinyl amines, vinyl carbamates and dienes, was achieved by using Ru(ii)-Pheox catalysts. This catalytic system can function at a low catalyst loading (3 mol%)...

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Kotozaki M, Chanthamath S, Fujii T, et al. Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts. Chem Commun (Camb). 2018;54(40):5110-5113doi: 10.1039/c8cc02286k.
Kotozaki, M., Chanthamath, S., Fujii, T., Shibatomi, K., & Iwasa, S. (2018). Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts. Chemical communications (Cambridge, England), 54(40), 5110-5113. https://doi.org/10.1039/c8cc02286k
Kotozaki, Manato, et al. "Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts." Chemical communications (Cambridge, England) vol. 54,40 (2018): 5110-5113. doi: https://doi.org/10.1039/c8cc02286k
Kotozaki M, Chanthamath S, Fujii T, Shibatomi K, Iwasa S. Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts. Chem Commun (Camb). 2018 May 15;54(40):5110-5113. doi: 10.1039/c8cc02286k. PMID: 29717307.
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Aziridines versus vinyl carbamates from the direct amination of electron-withdrawing group-substituted trifluoromethyl enoates.

The Journal of organic chemistry

Fioravanti S, Colantoni D, Pellacani L, Tardella PA.
PMID: 15822999
J Org Chem. 2005 Apr 15;70(8):3296-8. doi: 10.1021/jo050044w.

Aza-MIRC (Michael-initiated ring closure) and C-H insertion products were obtained in the reactions of trifluoromethylated olefins with different nosyloxycarbamates by changing base and solvent. Aza-Michael addition products were not isolated. The presence and the position of the trifluoromethyl group...

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Fioravanti S, Colantoni D, Pellacani L, et al. Aziridines versus vinyl carbamates from the direct amination of electron-withdrawing group-substituted trifluoromethyl enoates. J Org Chem. 2005;70(8):3296-8doi: 10.1021/jo050044w.
Fioravanti, S., Colantoni, D., Pellacani, L., & Tardella, P. A. (2005). Aziridines versus vinyl carbamates from the direct amination of electron-withdrawing group-substituted trifluoromethyl enoates. The Journal of organic chemistry, 70(8), 3296-8. https://doi.org/10.1021/jo050044w
Fioravanti, Stefania, et al. "Aziridines versus vinyl carbamates from the direct amination of electron-withdrawing group-substituted trifluoromethyl enoates." The Journal of organic chemistry vol. 70,8 (2005): 3296-8. doi: https://doi.org/10.1021/jo050044w
Fioravanti S, Colantoni D, Pellacani L, Tardella PA. Aziridines versus vinyl carbamates from the direct amination of electron-withdrawing group-substituted trifluoromethyl enoates. J Org Chem. 2005 Apr 15;70(8):3296-8. doi: 10.1021/jo050044w. PMID: 15822999.
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Amination of CF3-enones with nosyloxycarbamates.

The Journal of organic chemistry

Colantoni D, Fioravanti S, Pellacani L, Tardella PA.
PMID: 16872225
J Org Chem. 2006 Aug 04;71(16):6295-7. doi: 10.1021/jo060915h.

CF3-enones showed a different reactivity in amination reactions with nosyloxycarbamates. 4-Oxazolines or vinyl carbamates were obtained as unique products depending on the nature of double-bond substituents and on the choice of carbamates and bases. Starting from trans-trifluoroacetyl olefins carrying...

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Colantoni D, Fioravanti S, Pellacani L, et al. Amination of CF3-enones with nosyloxycarbamates. J Org Chem. 2006;71(16):6295-7doi: 10.1021/jo060915h.
Colantoni, D., Fioravanti, S., Pellacani, L., & Tardella, P. A. (2006). Amination of CF3-enones with nosyloxycarbamates. The Journal of organic chemistry, 71(16), 6295-7. https://doi.org/10.1021/jo060915h
Colantoni, Daniele, et al. "Amination of CF3-enones with nosyloxycarbamates." The Journal of organic chemistry vol. 71,16 (2006): 6295-7. doi: https://doi.org/10.1021/jo060915h
Colantoni D, Fioravanti S, Pellacani L, Tardella PA. Amination of CF3-enones with nosyloxycarbamates. J Org Chem. 2006 Aug 04;71(16):6295-7. doi: 10.1021/jo060915h. PMID: 16872225.
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Ligand-Free Pd-Catalyzed Synthesis of 3-Allylbenzofurans by Merging Decarboxylative Allylation and Nucleophilic Cyclization.

The Journal of organic chemistry

Zhang J, Wang JY, Huang MH, Hao WJ, Tu XC, Tu SJ, Jiang B.
PMID: 32383594
J Org Chem. 2020 Jun 05;85(11):7036-7044. doi: 10.1021/acs.joc.0c00375. Epub 2020 May 19.

A new single Pd-catalyzed decarboxylative allylation-nucleophilic cyclization relay is reported by using α-alkynyl arylols and vinylethylene carbonates (or vinyl carbamates), and a wide range of 3-allyl benzofurans with generally good yields were stereoselectively synthesized under mild conditions, among which...

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Zhang J, Wang JY, Huang MH, et al. Ligand-Free Pd-Catalyzed Synthesis of 3-Allylbenzofurans by Merging Decarboxylative Allylation and Nucleophilic Cyclization. J Org Chem. 2020;85(11):7036-7044doi: 10.1021/acs.joc.0c00375.
Zhang, J., Wang, J. Y., Huang, M. H., Hao, W. J., Tu, X. C., Tu, S. J., & Jiang, B. (2020). Ligand-Free Pd-Catalyzed Synthesis of 3-Allylbenzofurans by Merging Decarboxylative Allylation and Nucleophilic Cyclization. The Journal of organic chemistry, 85(11), 7036-7044. https://doi.org/10.1021/acs.joc.0c00375
Zhang, Jie, et al. "Ligand-Free Pd-Catalyzed Synthesis of 3-Allylbenzofurans by Merging Decarboxylative Allylation and Nucleophilic Cyclization." The Journal of organic chemistry vol. 85,11 (2020): 7036-7044. doi: https://doi.org/10.1021/acs.joc.0c00375
Zhang J, Wang JY, Huang MH, Hao WJ, Tu XC, Tu SJ, Jiang B. Ligand-Free Pd-Catalyzed Synthesis of 3-Allylbenzofurans by Merging Decarboxylative Allylation and Nucleophilic Cyclization. J Org Chem. 2020 Jun 05;85(11):7036-7044. doi: 10.1021/acs.joc.0c00375. Epub 2020 May 19. PMID: 32383594.
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Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes.

Angewandte Chemie (International ed. in English)

Zhang QL, Xiong Q, Li MM, Xiong W, Shi B, Lan Y, Lu LQ, Xiao WJ.
PMID: 32372524
Angew Chem Int Ed Engl. 2020 Aug 10;59(33):14096-14100. doi: 10.1002/anie.202005313. Epub 2020 Jun 04.

Higher-order cycloadditions, particularly [8+2] cycloadditions, are a straightforward and efficient strategy for constructing significant medium-sized architectures. Typically, configuration-restrained conjugated systems are utilized as 8π-components for higher-order concerted cycloadditions. However, for this reason, 10-membered monocyclic skeletons have never been constructed...

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Zhang QL, Xiong Q, Li MM, et al. Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes. Angew Chem Int Ed Engl. 2020;59(33):14096-14100doi: 10.1002/anie.202005313.
Zhang, Q. L., Xiong, Q., Li, M. M., Xiong, W., Shi, B., Lan, Y., Lu, L. Q., & Xiao, W. J. (2020). Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes. Angewandte Chemie (International ed. in English), 59(33), 14096-14100. https://doi.org/10.1002/anie.202005313
Zhang, Qun-Liang, et al. "Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes." Angewandte Chemie (International ed. in English) vol. 59,33 (2020): 14096-14100. doi: https://doi.org/10.1002/anie.202005313
Zhang QL, Xiong Q, Li MM, Xiong W, Shi B, Lan Y, Lu LQ, Xiao WJ. Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes. Angew Chem Int Ed Engl. 2020 Aug 10;59(33):14096-14100. doi: 10.1002/anie.202005313. Epub 2020 Jun 04. PMID: 32372524.
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Palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene: preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines.

Chemical communications (Cambridge, England)

Liu Q, Liu TX, Ru Y, Zhu X, Zhang G.
PMID: 31729498
Chem Commun (Camb). 2019 Nov 28;55(96):14498-14501. doi: 10.1039/c9cc07950e.

A general and practical methodology for the preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines through palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene with vinylethylene/2-alkylidenetrimethylene carbonates and vinyl carbamates was developed. Without additives or ligands, the Pd(PPh3)4-catalyzed transformations undergo decarboxylative O- and N-heteroannulation...

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Liu Q, Liu TX, Ru Y, et al. Palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene: preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines. Chem Commun (Camb). 2019;55(96):14498-14501doi: 10.1039/c9cc07950e.
Liu, Q., Liu, T. X., Ru, Y., Zhu, X., & Zhang, G. (2019). Palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene: preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines. Chemical communications (Cambridge, England), 55(96), 14498-14501. https://doi.org/10.1039/c9cc07950e
Liu, Qingfeng, et al. "Palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene: preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines." Chemical communications (Cambridge, England) vol. 55,96 (2019): 14498-14501. doi: https://doi.org/10.1039/c9cc07950e
Liu Q, Liu TX, Ru Y, Zhu X, Zhang G. Palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene: preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines. Chem Commun (Camb). 2019 Nov 28;55(96):14498-14501. doi: 10.1039/c9cc07950e. PMID: 31729498.
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Depolymerizable Poly(O-vinyl carbamate-.

ACS macro letters

Kumar K, Castaño EJ, Weidner AR, Yildirim A, Goodwin AP.
PMID: 28480130
ACS Macro Lett. 2016 May 17;5(5):636-640. doi: 10.1021/acsmacrolett.6b00219. Epub 2016 May 04.

Interest in stimulus responsive materials and polymers has grown over the years, having shown great promise in a diverse set of applications. For drug delivery, stimulus-responsive polymers have been shown to encapsulate therapeutic cargo such as small molecule drugs...

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Kumar K, Castaño EJ, Weidner AR, et al. Depolymerizable Poly(O-vinyl carbamate-. ACS Macro Lett. 2016;5(5):636-640doi: 10.1021/acsmacrolett.6b00219.
Kumar, K., Castaño, E. J., Weidner, A. R., Yildirim, A., & Goodwin, A. P. (2016). Depolymerizable Poly(O-vinyl carbamate-. ACS macro letters, 5(5), 636-640. https://doi.org/10.1021/acsmacrolett.6b00219
Kumar, Kaushlendra, et al. "Depolymerizable Poly(O-vinyl carbamate-." ACS macro letters vol. 5,5 (2016): 636-640. doi: https://doi.org/10.1021/acsmacrolett.6b00219
Kumar K, Castaño EJ, Weidner AR, Yildirim A, Goodwin AP. Depolymerizable Poly(O-vinyl carbamate-. ACS Macro Lett. 2016 May 17;5(5):636-640. doi: 10.1021/acsmacrolett.6b00219. Epub 2016 May 04. PMID: 28480130; PMCID: PMC5417698.
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Showing 1 to 10 of 10 entries