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Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones.

Organic letters

Wang Q, Huang L, Wu X, Jiang H.
PMID: 24237319
Org Lett. 2013 Dec 06;15(23):5940-3. doi: 10.1021/ol4027683. Epub 2013 Nov 15.

A simple and efficient palladium-catalyzed oxidative coupling between 2-alkynyl anilines and allylic alcohols is described by using cheap and green dioxygen as the oxidant. These cross-couplings have a large functional group tolerance and are of higher reactivity toward electron...

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Wang Q, Huang L, Wu X, et al. Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones. Org Lett. 2013;15(23):5940-3doi: 10.1021/ol4027683.
Wang, Q., Huang, L., Wu, X., & Jiang, H. (2013). Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones. Organic letters, 15(23), 5940-3. https://doi.org/10.1021/ol4027683
Wang, Qian, et al. "Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones." Organic letters vol. 15,23 (2013): 5940-3. doi: https://doi.org/10.1021/ol4027683
Wang Q, Huang L, Wu X, Jiang H. Nucleopalladation triggering the oxidative Heck reaction: a general strategy to diverse β-indole ketones. Org Lett. 2013 Dec 06;15(23):5940-3. doi: 10.1021/ol4027683. Epub 2013 Nov 15. PMID: 24237319.
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Highly Convergent Synthesis of Intensively Blue Emissive Furo[2,3-c]isoquinolines by a Palladium-Catalyzed Cyclization Cascade of Unsaturated Ugi Products.

Chemistry (Weinheim an der Bergstrasse, Germany)

Moni L, Gers-Panther CF, Anselmo M, Müller TJ, Riva R.
PMID: 26748452
Chemistry. 2016 Feb;22(6):2020-2031. doi: 10.1002/chem.201504335. Epub 2016 Jan 08.

A convergent and diversity-oriented approach to the unusual furo[2,3-c]isoquinoline scaffold is presented. This serendipity-driven approach is characterized by an Ugi multicomponent reaction, which gives the substrate for a palladium-catalyzed insertion-alkynylation-cycloisomerization cascade to provide the furo[2,3-c]isoquinolines in moderate to high...

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Moni L, Gers-Panther CF, Anselmo M, et al. Highly Convergent Synthesis of Intensively Blue Emissive Furo[2,3-c]isoquinolines by a Palladium-Catalyzed Cyclization Cascade of Unsaturated Ugi Products. Chemistry. 2016;22(6):2020-2031doi: 10.1002/chem.201504335.
Moni, L., Gers-Panther, C. F., Anselmo, M., Müller, T. J., & Riva, R. (2016). Highly Convergent Synthesis of Intensively Blue Emissive Furo[2,3-c]isoquinolines by a Palladium-Catalyzed Cyclization Cascade of Unsaturated Ugi Products. Chemistry (Weinheim an der Bergstrasse, Germany), 22(6), 2020-2031. https://doi.org/10.1002/chem.201504335
Moni, Lisa, et al. "Highly Convergent Synthesis of Intensively Blue Emissive Furo[2,3-c]isoquinolines by a Palladium-Catalyzed Cyclization Cascade of Unsaturated Ugi Products." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,6 (2016): 2020-2031. doi: https://doi.org/10.1002/chem.201504335
Moni L, Gers-Panther CF, Anselmo M, Müller TJ, Riva R. Highly Convergent Synthesis of Intensively Blue Emissive Furo[2,3-c]isoquinolines by a Palladium-Catalyzed Cyclization Cascade of Unsaturated Ugi Products. Chemistry. 2016 Feb;22(6):2020-2031. doi: 10.1002/chem.201504335. Epub 2016 Jan 08. PMID: 26748452.
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2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19.

ACS medicinal chemistry letters

Mallinger A, Schiemann K, Rink C, Sejberg J, Honey MA, Czodrowski P, Stubbs M, Poeschke O, Busch M, Schneider R, Schwarz D, Musil D, Burke R, Urbahns K, Workman P, Wienke D, Clarke PA, Raynaud FI, Eccles SA, Esdar C, Rohdich F, Blagg J.
PMID: 27326329
ACS Med Chem Lett. 2016 Mar 28;7(6):573-8. doi: 10.1021/acsmedchemlett.6b00022. eCollection 2016 Jun 09.

We demonstrate a designed scaffold-hop approach to the discovery of 2,8-disubstituted-1,6-naphthyridine- and 4,6-disubstituted-isoquinoline-based dual CDK8/19 ligands. Optimized compounds in both series exhibited rapid aldehyde oxidase-mediated metabolism, which could be abrogated by introduction of an amino substituent at C5 of...

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Mallinger A, Schiemann K, Rink C, et al. 2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19. ACS Med Chem Lett. 2016;7(6):573-8doi: 10.1021/acsmedchemlett.6b00022.
Mallinger, A., Schiemann, K., Rink, C., Sejberg, J., Honey, M. A., Czodrowski, P., Stubbs, M., Poeschke, O., Busch, M., Schneider, R., Schwarz, D., Musil, D., Burke, R., Urbahns, K., Workman, P., Wienke, D., Clarke, P. A., Raynaud, F. I., Eccles, S. A., Esdar, C., Rohdich, F., & Blagg, J. (2016). 2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19. ACS medicinal chemistry letters, 7(6), 573-8. https://doi.org/10.1021/acsmedchemlett.6b00022
Mallinger, Aurélie, et al. "2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19." ACS medicinal chemistry letters vol. 7,6 (2016): 573-8. doi: https://doi.org/10.1021/acsmedchemlett.6b00022
Mallinger A, Schiemann K, Rink C, Sejberg J, Honey MA, Czodrowski P, Stubbs M, Poeschke O, Busch M, Schneider R, Schwarz D, Musil D, Burke R, Urbahns K, Workman P, Wienke D, Clarke PA, Raynaud FI, Eccles SA, Esdar C, Rohdich F, Blagg J. 2,8-Disubstituted-1,6-Naphthyridines and 4,6-Disubstituted-Isoquinolines with Potent, Selective Affinity for CDK8/19. ACS Med Chem Lett. 2016 Mar 28;7(6):573-8. doi: 10.1021/acsmedchemlett.6b00022. eCollection 2016 Jun 09. PMID: 27326329; PMCID: PMC4904262.
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Synthesis of isoquinolines via Rh-catalyzed C-H activation/C-N cyclization with diazodiesters or diazoketoesters as a C2 source.

Organic & biomolecular chemistry

Wang J, Zha S, Chen K, Zhang F, Zhu J.
PMID: 27146107
Org Biomol Chem. 2016 Jun 07;14(21):4848-52. doi: 10.1039/c6ob00901h. Epub 2016 May 05.

Synthesis of isoquinolines based on efficient C-C and C-N bond formation through Rh(iii)-catalyzed C-H activation and subsequent intramolecular cyclization is reported. Diazodiesters serving as a C2 source in the newly formed heterocycles are first demonstrated. Additionally, the Rh(iii)-catalyzed direct...

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Wang J, Zha S, Chen K, et al. Synthesis of isoquinolines via Rh-catalyzed C-H activation/C-N cyclization with diazodiesters or diazoketoesters as a C2 source. Org Biomol Chem. 2016;14(21):4848-52doi: 10.1039/c6ob00901h.
Wang, J., Zha, S., Chen, K., Zhang, F., & Zhu, J. (2016). Synthesis of isoquinolines via Rh-catalyzed C-H activation/C-N cyclization with diazodiesters or diazoketoesters as a C2 source. Organic & biomolecular chemistry, 14(21), 4848-52. https://doi.org/10.1039/c6ob00901h
Wang, Jie, et al. "Synthesis of isoquinolines via Rh-catalyzed C-H activation/C-N cyclization with diazodiesters or diazoketoesters as a C2 source." Organic & biomolecular chemistry vol. 14,21 (2016): 4848-52. doi: https://doi.org/10.1039/c6ob00901h
Wang J, Zha S, Chen K, Zhang F, Zhu J. Synthesis of isoquinolines via Rh-catalyzed C-H activation/C-N cyclization with diazodiesters or diazoketoesters as a C2 source. Org Biomol Chem. 2016 Jun 07;14(21):4848-52. doi: 10.1039/c6ob00901h. Epub 2016 May 05. PMID: 27146107.
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1,3-Dipolar cycloadditions of azomethine imines.

Organic & biomolecular chemistry

Nájera C, Sansano JM, Yus M.
PMID: 26140443
Org Biomol Chem. 2015 Aug 28;13(32):8596-636. doi: 10.1039/c5ob01086a. Epub 2015 Jul 03.

Azomethine imines are considered 1,3-dipoles of the aza-allyl type which are transient intermediates and should be generated in situ but can also be stable and isolable compounds. They react with electron-rich and electron-poor olefins as well as with acetylenic...

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Nájera C, Sansano JM, Yus M. 1,3-Dipolar cycloadditions of azomethine imines. Org Biomol Chem. 2015;13(32):8596-636doi: 10.1039/c5ob01086a.
Nájera, C., Sansano, J. M., & Yus, M. (2015). 1,3-Dipolar cycloadditions of azomethine imines. Organic & biomolecular chemistry, 13(32), 8596-636. https://doi.org/10.1039/c5ob01086a
Nájera, Carmen, et al. "1,3-Dipolar cycloadditions of azomethine imines." Organic & biomolecular chemistry vol. 13,32 (2015): 8596-636. doi: https://doi.org/10.1039/c5ob01086a
Nájera C, Sansano JM, Yus M. 1,3-Dipolar cycloadditions of azomethine imines. Org Biomol Chem. 2015 Aug 28;13(32):8596-636. doi: 10.1039/c5ob01086a. Epub 2015 Jul 03. PMID: 26140443.
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Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines.

The Journal of organic chemistry

Zhao Y, Jin J, Boyle JW, Lee BR, Day DP, Susanti D, Clarkson GJ, Chan PW.
PMID: 28225621
J Org Chem. 2017 Mar 17;82(6):2826-2834. doi: 10.1021/acs.joc.7b00048. Epub 2017 Mar 07.

A synthetic method to prepare partially hydrogenated isoquinolines efficiently from silver-mediated [3,3]-sigmatropic rearrangement/Diels-Alder reaction of 1,9-dien-4-yne esters is described. The reactions were shown to be robust with a wide variety of substitution patterns tolerated to provide the corresponding nitrogen-containing...

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Zhao Y, Jin J, Boyle JW, et al. Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines. J Org Chem. 2017;82(6):2826-2834doi: 10.1021/acs.joc.7b00048.
Zhao, Y., Jin, J., Boyle, J. W., Lee, B. R., Day, D. P., Susanti, D., Clarkson, G. J., & Chan, P. W. (2017). Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines. The Journal of organic chemistry, 82(6), 2826-2834. https://doi.org/10.1021/acs.joc.7b00048
Zhao, Yichao, et al. "Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines." The Journal of organic chemistry vol. 82,6 (2017): 2826-2834. doi: https://doi.org/10.1021/acs.joc.7b00048
Zhao Y, Jin J, Boyle JW, Lee BR, Day DP, Susanti D, Clarkson GJ, Chan PW. Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines. J Org Chem. 2017 Mar 17;82(6):2826-2834. doi: 10.1021/acs.joc.7b00048. Epub 2017 Mar 07. PMID: 28225621.
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A practical and efficient approach to imidazo[1,2-.

Beilstein journal of organic chemistry

Shao T, Gong Z, Su T, Hao W, Che C.
PMID: 28546839
Beilstein J Org Chem. 2017 May 04;13:817-824. doi: 10.3762/bjoc.13.82. eCollection 2017.

Diversity-oriented synthesis of the biologically intriguing imidazo[1,2-

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Shao T, Gong Z, Su T, et al. A practical and efficient approach to imidazo[1,2-. Beilstein J Org Chem. 2017;13:817-824doi: 10.3762/bjoc.13.82.
Shao, T., Gong, Z., Su, T., Hao, W., & Che, C. (2017). A practical and efficient approach to imidazo[1,2-. Beilstein journal of organic chemistry, 13817-824. https://doi.org/10.3762/bjoc.13.82
Shao, Taofeng, et al. "A practical and efficient approach to imidazo[1,2-." Beilstein journal of organic chemistry vol. 13 (2017): 817-824. doi: https://doi.org/10.3762/bjoc.13.82
Shao T, Gong Z, Su T, Hao W, Che C. A practical and efficient approach to imidazo[1,2-. Beilstein J Org Chem. 2017 May 04;13:817-824. doi: 10.3762/bjoc.13.82. eCollection 2017. PMID: 28546839; PMCID: PMC5433183.
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Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization.

Organic letters

Parthasarathy K, Azcargorta AR, Cheng Y, Bolm C.
PMID: 24720665
Org Lett. 2014 May 02;16(9):2538-41. doi: 10.1021/ol500918t. Epub 2014 Apr 11.

Rhodium-catalyzed C-H functionalizations have been used for ortho-directed additions of 2-arylpyridines and (hetero)aryl-substituted pyrimidines, isoquinolines, and benzo[h]quinolones to cyclic imines. The resulting amino-functionalized products are formed in good to high yields.

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Parthasarathy K, Azcargorta AR, Cheng Y, et al. Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization. Org Lett. 2014;16(9):2538-41doi: 10.1021/ol500918t.
Parthasarathy, K., Azcargorta, A. R., Cheng, Y., & Bolm, C. (2014). Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization. Organic letters, 16(9), 2538-41. https://doi.org/10.1021/ol500918t
Parthasarathy, Kanniyappan, et al. "Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization." Organic letters vol. 16,9 (2014): 2538-41. doi: https://doi.org/10.1021/ol500918t
Parthasarathy K, Azcargorta AR, Cheng Y, Bolm C. Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization. Org Lett. 2014 May 02;16(9):2538-41. doi: 10.1021/ol500918t. Epub 2014 Apr 11. PMID: 24720665.
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Rh(iii)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines.

Organic & biomolecular chemistry

Chen R, Qi J, Mao Z, Cui S.
PMID: 27273816
Org Biomol Chem. 2016 Jul 14;14(26):6201-4. doi: 10.1039/c6ob00942e. Epub 2016 Jun 08.

A Rh(iii)-catalyzed C-H activation/cyclization of oximes and alkenes for facile and regioselective access to isoquinolines has been developed. This protocol features mild reaction conditions and easily accessible starting materials, and has been applied to the concise synthesis of moxaverine....

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Chen R, Qi J, Mao Z, et al. Rh(iii)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines. Org Biomol Chem. 2016;14(26):6201-4doi: 10.1039/c6ob00942e.
Chen, R., Qi, J., Mao, Z., & Cui, S. (2016). Rh(iii)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines. Organic & biomolecular chemistry, 14(26), 6201-4. https://doi.org/10.1039/c6ob00942e
Chen, Renjie, et al. "Rh(iii)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines." Organic & biomolecular chemistry vol. 14,26 (2016): 6201-4. doi: https://doi.org/10.1039/c6ob00942e
Chen R, Qi J, Mao Z, Cui S. Rh(iii)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines. Org Biomol Chem. 2016 Jul 14;14(26):6201-4. doi: 10.1039/c6ob00942e. Epub 2016 Jun 08. PMID: 27273816.
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Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines.

The Journal of organic chemistry

Zhang ZW, Lin A, Yang J.
PMID: 24992575
J Org Chem. 2014 Aug 01;79(15):7041-50. doi: 10.1021/jo5010586. Epub 2014 Jul 11.

Methyl ketone oxime esters have been found to be excellent coupling partners for C(sp(2))-C(sp(3)) bond formation via Pd-catalyzed aromatic C-H activation. This transformation forms the basis of an approach to regioselectively synthesize substituted isoquinolines via coupling with aryloxime esters....

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Zhang ZW, Lin A, Yang J. Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines. J Org Chem. 2014;79(15):7041-50doi: 10.1021/jo5010586.
Zhang, Z. W., Lin, A., & Yang, J. (2014). Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines. The Journal of organic chemistry, 79(15), 7041-50. https://doi.org/10.1021/jo5010586
Zhang, Zhi-Wei, et al. "Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines." The Journal of organic chemistry vol. 79,15 (2014): 7041-50. doi: https://doi.org/10.1021/jo5010586
Zhang ZW, Lin A, Yang J. Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines. J Org Chem. 2014 Aug 01;79(15):7041-50. doi: 10.1021/jo5010586. Epub 2014 Jul 11. PMID: 24992575.
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Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds.

The Journal of organic chemistry

Li XG, Sun M, Jin Q, Liu K, Liu PN.
PMID: 27042947
J Org Chem. 2016 May 06;81(9):3901-10. doi: 10.1021/acs.joc.6b00264. Epub 2016 Apr 13.

A Rh(III)-catalyzed coupling/cyclization cascade reaction is described, which involves arylimidates and diazo compounds and proceeds via intermolecular C-C bond formation and subsequent intramolecular C-N bond formation. Mechanistic investigation revealed that the reaction is a two-step process: the initial Rh(III)-catalyzed...

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Li XG, Sun M, Jin Q, et al. Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds. J Org Chem. 2016;81(9):3901-10doi: 10.1021/acs.joc.6b00264.
Li, X. G., Sun, M., Jin, Q., Liu, K., & Liu, P. N. (2016). Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds. The Journal of organic chemistry, 81(9), 3901-10. https://doi.org/10.1021/acs.joc.6b00264
Li, Xing Guang, et al. "Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds." The Journal of organic chemistry vol. 81,9 (2016): 3901-10. doi: https://doi.org/10.1021/acs.joc.6b00264
Li XG, Sun M, Jin Q, Liu K, Liu PN. Access to Isoquinolines and Isoquinolin-3-ols via Rh(III)-Catalyzed Coupling/Cyclization Cascade Reaction of Arylimidates and Diazo Compounds. J Org Chem. 2016 May 06;81(9):3901-10. doi: 10.1021/acs.joc.6b00264. Epub 2016 Apr 13. PMID: 27042947.
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Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Indium(III)-Promoted Halocyclizations of N-Propargylic Sulfonylhydrazones.

Organic letters

Li RH, Ding CK, Jiang YN, Ding ZC, An XM, Tang HT, Jing QW, Zhan ZP.
PMID: 26990932
Org Lett. 2016 Apr 01;18(7):1666-9. doi: 10.1021/acs.orglett.6b00534. Epub 2016 Mar 18.

A novel method for the preparation of 5,6-dihydropyrazolo[5,1-a]isoquinoline via indium(III)-promoted halocyclizations of N-propargylic sulfonylhydrazones has been developed. The pyrazole and 3,4-dihydroisoquinoline moieties were synchronously formed via a cascade cyclization reaction using easily assembled open-chain compounds. The pyrazole and 3,4-dihydroisoquinoline...

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Li RH, Ding CK, Jiang YN, et al. Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Indium(III)-Promoted Halocyclizations of N-Propargylic Sulfonylhydrazones. Org Lett. 2016;18(7):1666-9doi: 10.1021/acs.orglett.6b00534.
Li, R. H., Ding, C. K., Jiang, Y. N., Ding, Z. C., An, X. M., Tang, H. T., Jing, Q. W., & Zhan, Z. P. (2016). Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Indium(III)-Promoted Halocyclizations of N-Propargylic Sulfonylhydrazones. Organic letters, 18(7), 1666-9. https://doi.org/10.1021/acs.orglett.6b00534
Li, Ren-Hao, et al. "Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Indium(III)-Promoted Halocyclizations of N-Propargylic Sulfonylhydrazones." Organic letters vol. 18,7 (2016): 1666-9. doi: https://doi.org/10.1021/acs.orglett.6b00534
Li RH, Ding CK, Jiang YN, Ding ZC, An XM, Tang HT, Jing QW, Zhan ZP. Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Indium(III)-Promoted Halocyclizations of N-Propargylic Sulfonylhydrazones. Org Lett. 2016 Apr 01;18(7):1666-9. doi: 10.1021/acs.orglett.6b00534. Epub 2016 Mar 18. PMID: 26990932.
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