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Enantioselective cyclization of alkene radical cations.

Organic letters

Crich D, Shirai M, Rumthao S.
PMID: 14507226
Org Lett. 2003 Oct 02;5(20):3767-9. doi: 10.1021/ol035564x.

[reaction: see text] Enantiomerically enriched beta-(diphenylphosphatoxy)nitroalkanes undergo radical ionic fragmentation, induced by tributyltin hydride and AIBN in benzene at reflux, to give alkene radical cations in contact radical ion pairs. These contact ion pairs are trapped intramolecularly by amines...

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Crich D, Shirai M, Rumthao S. Enantioselective cyclization of alkene radical cations. Org Lett. 2003;5(20):3767-9doi: 10.1021/ol035564x.
Crich, D., Shirai, M., & Rumthao, S. (2003). Enantioselective cyclization of alkene radical cations. Organic letters, 5(20), 3767-9. https://doi.org/10.1021/ol035564x
Crich, David, et al. "Enantioselective cyclization of alkene radical cations." Organic letters vol. 5,20 (2003): 3767-9. doi: https://doi.org/10.1021/ol035564x
Crich D, Shirai M, Rumthao S. Enantioselective cyclization of alkene radical cations. Org Lett. 2003 Oct 02;5(20):3767-9. doi: 10.1021/ol035564x. PMID: 14507226.
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Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts.

Chemical communications (Cambridge, England)

Hussein L, Purkait N, Biyikal M, Tausch E, Roesky PW, Blechert S.
PMID: 24592399
Chem Commun (Camb). 2014 Apr 14;50(29):3862-4. doi: 10.1039/c3cc48874h.

New bimetallic Zn/Zr salen-type systems were employed as catalysts in the asymmetric intramolecular hydroamination reaction. High enantioselectivity for the formation of piperidines of up to 98% ee were observed.

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Hussein L, Purkait N, Biyikal M, et al. Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts. Chem Commun (Camb). 2014;50(29):3862-4doi: 10.1039/c3cc48874h.
Hussein, L., Purkait, N., Biyikal, M., Tausch, E., Roesky, P. W., & Blechert, S. (2014). Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts. Chemical communications (Cambridge, England), 50(29), 3862-4. https://doi.org/10.1039/c3cc48874h
Hussein, Lenard, et al. "Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts." Chemical communications (Cambridge, England) vol. 50,29 (2014): 3862-4. doi: https://doi.org/10.1039/c3cc48874h
Hussein L, Purkait N, Biyikal M, Tausch E, Roesky PW, Blechert S. Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts. Chem Commun (Camb). 2014 Apr 14;50(29):3862-4. doi: 10.1039/c3cc48874h. PMID: 24592399.
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Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles.

Beilstein journal of organic chemistry

Jakubec P, Cockfield DM, Helliwell M, Raftery J, Dixon DJ.
PMID: 22563355
Beilstein J Org Chem. 2012;8:567-78. doi: 10.3762/bjoc.8.64. Epub 2012 Apr 16.

A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with...

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Jakubec P, Cockfield DM, Helliwell M, et al. Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles. Beilstein J Org Chem. 2012;8:567-78doi: 10.3762/bjoc.8.64.
Jakubec, P., Cockfield, D. M., Helliwell, M., Raftery, J., & Dixon, D. J. (2012). Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles. Beilstein journal of organic chemistry, 8567-78. https://doi.org/10.3762/bjoc.8.64
Jakubec, Pavol, et al. "Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles." Beilstein journal of organic chemistry vol. 8 (2012): 567-78. doi: https://doi.org/10.3762/bjoc.8.64
Jakubec P, Cockfield DM, Helliwell M, Raftery J, Dixon DJ. Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles. Beilstein J Org Chem. 2012;8:567-78. doi: 10.3762/bjoc.8.64. Epub 2012 Apr 16. PMID: 22563355; PMCID: PMC3343283.
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Stereoselective Synthesis of Piperidines by Iridium-Catalyzed Cyclocondensation.

Angewandte Chemie (International ed. in English)

Sandmeier T, Krautwald S, Carreira EM.
PMID: 28731546
Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11515-11519. doi: 10.1002/anie.201706374. Epub 2017 Aug 07.

An iridium-catalyzed cyclocondensation of amino alcohols and aldehydes is reported. Intramolecular allylic substitution by an enamine intermediate and subsequent in situ reduction furnishes 3,4-disubstituted piperidines with high enantiospecificity and good diastereoselectivity. The modular approach and the broad functional group...

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Sandmeier T, Krautwald S, Carreira EM. Stereoselective Synthesis of Piperidines by Iridium-Catalyzed Cyclocondensation. Angew Chem Int Ed Engl. 2017;56(38):11515-11519doi: 10.1002/anie.201706374.
Sandmeier, T., Krautwald, S., & Carreira, E. M. (2017). Stereoselective Synthesis of Piperidines by Iridium-Catalyzed Cyclocondensation. Angewandte Chemie (International ed. in English), 56(38), 11515-11519. https://doi.org/10.1002/anie.201706374
Sandmeier, Tobias, et al. "Stereoselective Synthesis of Piperidines by Iridium-Catalyzed Cyclocondensation." Angewandte Chemie (International ed. in English) vol. 56,38 (2017): 11515-11519. doi: https://doi.org/10.1002/anie.201706374
Sandmeier T, Krautwald S, Carreira EM. Stereoselective Synthesis of Piperidines by Iridium-Catalyzed Cyclocondensation. Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11515-11519. doi: 10.1002/anie.201706374. Epub 2017 Aug 07. PMID: 28731546.
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The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process.

Nature chemistry

Nairoukh Z, Wollenburg M, Schlepphorst C, Bergander K, Glorius F.
PMID: 30664720
Nat Chem. 2019 Mar;11(3):264-270. doi: 10.1038/s41557-018-0197-2. Epub 2019 Jan 21.

Piperidines and fluorine substituents are both independently indispensable components in pharmaceuticals, agrochemicals and materials. Logically, the incorporation of fluorine atoms into piperidine scaffolds is therefore an area of tremendous potential. However, synthetic approaches towards the formation of these architectures...

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Nairoukh Z, Wollenburg M, Schlepphorst C, et al. The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process. Nat Chem. 2019;11(3):264-270doi: 10.1038/s41557-018-0197-2.
Nairoukh, Z., Wollenburg, M., Schlepphorst, C., Bergander, K., & Glorius, F. (2019). The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process. Nature chemistry, 11(3), 264-270. https://doi.org/10.1038/s41557-018-0197-2
Nairoukh, Zackaria, et al. "The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process." Nature chemistry vol. 11,3 (2019): 264-270. doi: https://doi.org/10.1038/s41557-018-0197-2
Nairoukh Z, Wollenburg M, Schlepphorst C, Bergander K, Glorius F. The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process. Nat Chem. 2019 Mar;11(3):264-270. doi: 10.1038/s41557-018-0197-2. Epub 2019 Jan 21. PMID: 30664720; PMCID: PMC6522351.
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Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds.

Journal of the American Chemical Society

Ryan J, Šiaučiulis M, Gomm A, Maciá B, O'Reilly E, Caprio V.
PMID: 27960354
J Am Chem Soc. 2016 Dec 14;138(49):15798-15800. doi: 10.1021/jacs.6b07024. Epub 2016 Nov 23.

The expanding "toolbox" of biocatalysts opens new opportunities to redesign synthetic strategies to target molecules by incorporating a key enzymatic step into the synthesis. Herein, we describe a general biocatalytic approach for the enantioselective preparation of 2,6-disubstituted piperidines starting...

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Ryan J, Šiaučiulis M, Gomm A, et al. Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds. J Am Chem Soc. 2016;138(49):15798-15800doi: 10.1021/jacs.6b07024.
Ryan, J., Šiaučiulis, M., Gomm, A., Maciá, B., O'Reilly, E., & Caprio, V. (2016). Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds. Journal of the American Chemical Society, 138(49), 15798-15800. https://doi.org/10.1021/jacs.6b07024
Ryan, James, et al. "Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds." Journal of the American Chemical Society vol. 138,49 (2016): 15798-15800. doi: https://doi.org/10.1021/jacs.6b07024
Ryan J, Šiaučiulis M, Gomm A, Maciá B, O'Reilly E, Caprio V. Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds. J Am Chem Soc. 2016 Dec 14;138(49):15798-15800. doi: 10.1021/jacs.6b07024. Epub 2016 Nov 23. PMID: 27960354.
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Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines.

Organic & biomolecular chemistry

Yan N, Fang Z, Liu QQ, Guo XH, Hu XG.
PMID: 26971837
Org Biomol Chem. 2016 Apr 07;14(13):3469-75. doi: 10.1039/c6ob00063k. Epub 2016 Mar 14.

Utilizing molecular conformation as a controlling factor, epoxide-containing 2-aryl-piperidines can be ring-opened with the reagent combination of tetrabutylammonium fluoride (TBAF) and potassium bifluoride (KHF2) in a regioselective and divergent fashion. Four different types of hydroxylated fluoro-piperidines, valuable building blocks...

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Yan N, Fang Z, Liu QQ, et al. Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines. Org Biomol Chem. 2016;14(13):3469-75doi: 10.1039/c6ob00063k.
Yan, N., Fang, Z., Liu, Q. Q., Guo, X. H., & Hu, X. G. (2016). Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines. Organic & biomolecular chemistry, 14(13), 3469-75. https://doi.org/10.1039/c6ob00063k
Yan, Nan, et al. "Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines." Organic & biomolecular chemistry vol. 14,13 (2016): 3469-75. doi: https://doi.org/10.1039/c6ob00063k
Yan N, Fang Z, Liu QQ, Guo XH, Hu XG. Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines. Org Biomol Chem. 2016 Apr 07;14(13):3469-75. doi: 10.1039/c6ob00063k. Epub 2016 Mar 14. PMID: 26971837.
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Pd-Catalyzed Carboamination of Alkylidenecyclopropanes: Synthesis of Congested Pyrrolidines and Piperidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Lazzara PR, Fitzpatrick KP, Eichman CC.
PMID: 27661456
Chemistry. 2016 Nov 14;22(47):16779-16782. doi: 10.1002/chem.201604077. Epub 2016 Oct 11.

The synthesis of densely functionalized N-heterocycles is an ongoing challenge in chemical synthesis. Herein, we report an efficient method for the construction of pyrrolidine and piperidine scaffolds using a palladium-catalyzed carboamination of alkylidenecyclopropanes.

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Lazzara PR, Fitzpatrick KP, Eichman CC. Pd-Catalyzed Carboamination of Alkylidenecyclopropanes: Synthesis of Congested Pyrrolidines and Piperidines. Chemistry. 2016;22(47):16779-16782doi: 10.1002/chem.201604077.
Lazzara, P. R., Fitzpatrick, K. P., & Eichman, C. C. (2016). Pd-Catalyzed Carboamination of Alkylidenecyclopropanes: Synthesis of Congested Pyrrolidines and Piperidines. Chemistry (Weinheim an der Bergstrasse, Germany), 22(47), 16779-16782. https://doi.org/10.1002/chem.201604077
Lazzara, Phillip R, et al. "Pd-Catalyzed Carboamination of Alkylidenecyclopropanes: Synthesis of Congested Pyrrolidines and Piperidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,47 (2016): 16779-16782. doi: https://doi.org/10.1002/chem.201604077
Lazzara PR, Fitzpatrick KP, Eichman CC. Pd-Catalyzed Carboamination of Alkylidenecyclopropanes: Synthesis of Congested Pyrrolidines and Piperidines. Chemistry. 2016 Nov 14;22(47):16779-16782. doi: 10.1002/chem.201604077. Epub 2016 Oct 11. PMID: 27661456.
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Site-Selective Alkenylation of δ-C(sp(3))-H Bonds with Alkynes via a Six-Membered Palladacycle.

Journal of the American Chemical Society

Xu JW, Zhang ZZ, Rao WH, Shi BF.
PMID: 27529372
J Am Chem Soc. 2016 Aug 31;138(34):10750-3. doi: 10.1021/jacs.6b05978. Epub 2016 Aug 18.

Most chelation-assisted aliphatic C-H activation proceeds through a kinetically favored five-membered cyclometalated intermediate. Here, we report the first site-selective alkenylation of δ-C(sp(3))-H in the presence of more accessible γ-C(sp(3))-H bonds via a kinetically less favored six-membered palladacycle. A wide...

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Xu JW, Zhang ZZ, Rao WH, et al. Site-Selective Alkenylation of δ-C(sp(3))-H Bonds with Alkynes via a Six-Membered Palladacycle. J Am Chem Soc. 2016;138(34):10750-3doi: 10.1021/jacs.6b05978.
Xu, J. W., Zhang, Z. Z., Rao, W. H., & Shi, B. F. (2016). Site-Selective Alkenylation of δ-C(sp(3))-H Bonds with Alkynes via a Six-Membered Palladacycle. Journal of the American Chemical Society, 138(34), 10750-3. https://doi.org/10.1021/jacs.6b05978
Xu, Jing-Wen, et al. "Site-Selective Alkenylation of δ-C(sp(3))-H Bonds with Alkynes via a Six-Membered Palladacycle." Journal of the American Chemical Society vol. 138,34 (2016): 10750-3. doi: https://doi.org/10.1021/jacs.6b05978
Xu JW, Zhang ZZ, Rao WH, Shi BF. Site-Selective Alkenylation of δ-C(sp(3))-H Bonds with Alkynes via a Six-Membered Palladacycle. J Am Chem Soc. 2016 Aug 31;138(34):10750-3. doi: 10.1021/jacs.6b05978. Epub 2016 Aug 18. PMID: 27529372.
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[Co(TPP)]-Catalyzed Formation of Substituted Piperidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Lankelma M, Olivares AM, de Bruin B.
PMID: 30844097
Chemistry. 2019 Apr 17;25(22):5658-5663. doi: 10.1002/chem.201900587. Epub 2019 Apr 01.

Radical cyclization via cobalt(III)-carbene radical intermediates is a powerful method for the synthesis of (hetero)cyclic structures. Building on the recently reported synthesis of five-membered N-heterocyclic pyrrolidines catalyzed by Co

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Lankelma M, Olivares AM, de Bruin B. [Co(TPP)]-Catalyzed Formation of Substituted Piperidines. Chemistry. 2019;25(22):5658-5663doi: 10.1002/chem.201900587.
Lankelma, M., Olivares, A. M., & de Bruin, B. (2019). [Co(TPP)]-Catalyzed Formation of Substituted Piperidines. Chemistry (Weinheim an der Bergstrasse, Germany), 25(22), 5658-5663. https://doi.org/10.1002/chem.201900587
Lankelma, Marianne, et al. "[Co(TPP)]-Catalyzed Formation of Substituted Piperidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 25,22 (2019): 5658-5663. doi: https://doi.org/10.1002/chem.201900587
Lankelma M, Olivares AM, de Bruin B. [Co(TPP)]-Catalyzed Formation of Substituted Piperidines. Chemistry. 2019 Apr 17;25(22):5658-5663. doi: 10.1002/chem.201900587. Epub 2019 Apr 01. PMID: 30844097; PMCID: PMC6563703.
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Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles.

Angewandte Chemie (International ed. in English)

Yedoyan J, Wurzer N, Klimczak U, Ertl T, Reiser O.
PMID: 30629786
Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3594-3598. doi: 10.1002/anie.201813716. Epub 2019 Feb 04.

A palladium-catalyzed coupling between aryl halides and monocyclopropanated pyrroles or furans has been developed, leading to valuable six-membered N- and O-heterocycles. As the key step, a selective cleavage of the non-activated endocyclic C-C bond of the 2-heterobicyclo-[3.1.0]hexane framework is...

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Yedoyan J, Wurzer N, Klimczak U, et al. Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles. Angew Chem Int Ed Engl. 2019;58(11):3594-3598doi: 10.1002/anie.201813716.
Yedoyan, J., Wurzer, N., Klimczak, U., Ertl, T., & Reiser, O. (2019). Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles. Angewandte Chemie (International ed. in English), 58(11), 3594-3598. https://doi.org/10.1002/anie.201813716
Yedoyan, Julietta, et al. "Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles." Angewandte Chemie (International ed. in English) vol. 58,11 (2019): 3594-3598. doi: https://doi.org/10.1002/anie.201813716
Yedoyan J, Wurzer N, Klimczak U, Ertl T, Reiser O. Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles. Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3594-3598. doi: 10.1002/anie.201813716. Epub 2019 Feb 04. PMID: 30629786.
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Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions.

Organic & biomolecular chemistry

Guerola M, Escolano M, Alzuet-Piña G, Gómez-Bengoa E, Ramírez de Arellano C, Sánchez-Roselló M, Del Pozo C.
PMID: 29911720
Org Biomol Chem. 2018 Jul 07;16(25):4650-4658. doi: 10.1039/c8ob01139g. Epub 2018 Jun 18.

An organocatalytic enantioselective intramolecular aza-Michael reaction has been described for the first time in a desymmetrization process employing substrates different from cyclohexadienones. By using 9-amino-9-deoxy-epi-hydroquinine as the catalyst and trifluoroacetic acid as a co-catalyst, a series of enantiomerically enriched...

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Guerola M, Escolano M, Alzuet-Piña G, et al. Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions. Org Biomol Chem. 2018;16(25):4650-4658doi: 10.1039/c8ob01139g.
Guerola, M., Escolano, M., Alzuet-Piña, G., Gómez-Bengoa, E., Ramírez de Arellano, C., Sánchez-Roselló, M., & Del Pozo, C. (2018). Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions. Organic & biomolecular chemistry, 16(25), 4650-4658. https://doi.org/10.1039/c8ob01139g
Guerola, Marta, et al. "Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions." Organic & biomolecular chemistry vol. 16,25 (2018): 4650-4658. doi: https://doi.org/10.1039/c8ob01139g
Guerola M, Escolano M, Alzuet-Piña G, Gómez-Bengoa E, Ramírez de Arellano C, Sánchez-Roselló M, Del Pozo C. Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions. Org Biomol Chem. 2018 Jul 07;16(25):4650-4658. doi: 10.1039/c8ob01139g. Epub 2018 Jun 18. PMID: 29911720.
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