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One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the N-tosyl imine of chloroacetaldehyde with an asymmetric Mannich reaction as a key step.

Chemistry (Weinheim an der Bergstrasse, Germany)

Hayashi Y, Urushima T, Sakamoto D, Torii K, Ishikawa H.
PMID: 21887838
Chemistry. 2011 Oct 10;17(42):11715-8. doi: 10.1002/chem.201101668. Epub 2011 Sep 02.

No abstract available.

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Hayashi Y, Urushima T, Sakamoto D, et al. One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the N-tosyl imine of chloroacetaldehyde with an asymmetric Mannich reaction as a key step. Chemistry. 2011;17(42):11715-8doi: 10.1002/chem.201101668.
Hayashi, Y., Urushima, T., Sakamoto, D., Torii, K., & Ishikawa, H. (2011). One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the N-tosyl imine of chloroacetaldehyde with an asymmetric Mannich reaction as a key step. Chemistry (Weinheim an der Bergstrasse, Germany), 17(42), 11715-8. https://doi.org/10.1002/chem.201101668
Hayashi, Yujiro, et al. "One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the N-tosyl imine of chloroacetaldehyde with an asymmetric Mannich reaction as a key step." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 17,42 (2011): 11715-8. doi: https://doi.org/10.1002/chem.201101668
Hayashi Y, Urushima T, Sakamoto D, Torii K, Ishikawa H. One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the N-tosyl imine of chloroacetaldehyde with an asymmetric Mannich reaction as a key step. Chemistry. 2011 Oct 10;17(42):11715-8. doi: 10.1002/chem.201101668. Epub 2011 Sep 02. PMID: 21887838.
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Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp(3) )-H Activation.

Angewandte Chemie (International ed. in English)

Zakrzewski J, Smalley AP, Kabeshov MA, Gaunt MJ, Lapkin AA.
PMID: 27304395
Angew Chem Int Ed Engl. 2016 Jul 25;55(31):8878-83. doi: 10.1002/anie.201602483. Epub 2016 Jun 15.

A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp(3) )-H activation is described. The new flow reaction could be combined with an aziridine-ring-opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed...

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Zakrzewski J, Smalley AP, Kabeshov MA, et al. Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp(3) )-H Activation. Angew Chem Int Ed Engl. 2016;55(31):8878-83doi: 10.1002/anie.201602483.
Zakrzewski, J., Smalley, A. P., Kabeshov, M. A., Gaunt, M. J., & Lapkin, A. A. (2016). Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp(3) )-H Activation. Angewandte Chemie (International ed. in English), 55(31), 8878-83. https://doi.org/10.1002/anie.201602483
Zakrzewski, Jacek, et al. "Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp(3) )-H Activation." Angewandte Chemie (International ed. in English) vol. 55,31 (2016): 8878-83. doi: https://doi.org/10.1002/anie.201602483
Zakrzewski J, Smalley AP, Kabeshov MA, Gaunt MJ, Lapkin AA. Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp(3) )-H Activation. Angew Chem Int Ed Engl. 2016 Jul 25;55(31):8878-83. doi: 10.1002/anie.201602483. Epub 2016 Jun 15. PMID: 27304395; PMCID: PMC5094502.
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Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes.

ACS central science

Jiang J, Kuo CL, Wu L, Franke C, Kallemeijn WW, Florea BI, van Meel E, van der Marel GA, Codée JD, Boot RG, Davies GJ, Overkleeft HS, Aerts JM.
PMID: 27280170
ACS Cent Sci. 2016 May 25;2(5):351-8. doi: 10.1021/acscentsci.6b00057. Epub 2016 Apr 26.

The development of small molecule activity-based probes (ABPs) is an evolving and powerful area of chemistry. There is a major need for synthetically accessible and specific ABPs to advance our understanding of enzymes in health and disease. α-Glucosidases are...

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Jiang J, Kuo CL, Wu L, et al. Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes. ACS Cent Sci. 2016;2(5):351-8doi: 10.1021/acscentsci.6b00057.
Jiang, J., Kuo, C. L., Wu, L., Franke, C., Kallemeijn, W. W., Florea, B. I., van Meel, E., van der Marel, G. A., Codée, J. D., Boot, R. G., Davies, G. J., Overkleeft, H. S., & Aerts, J. M. (2016). Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes. ACS central science, 2(5), 351-8. https://doi.org/10.1021/acscentsci.6b00057
Jiang, Jianbing, et al. "Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes." ACS central science vol. 2,5 (2016): 351-8. doi: https://doi.org/10.1021/acscentsci.6b00057
Jiang J, Kuo CL, Wu L, Franke C, Kallemeijn WW, Florea BI, van Meel E, van der Marel GA, Codée JD, Boot RG, Davies GJ, Overkleeft HS, Aerts JM. Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes. ACS Cent Sci. 2016 May 25;2(5):351-8. doi: 10.1021/acscentsci.6b00057. Epub 2016 Apr 26. PMID: 27280170; PMCID: PMC4882745.
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Synthesis of functionalized amino epoxides by a three-component coupling involving aziridines, arynes and aldehydes.

Chemical communications (Cambridge, England)

Roy T, Thangaraj M, Gonnade RG, Biju AT.
PMID: 27400886
Chem Commun (Camb). 2016 Jul 12;52(58):9044-7. doi: 10.1039/c6cc00057f.

A transition-metal-free three-component coupling involving N-substituted aziridines, arynes and aldehydes resulting in the formation of trisubstituted N-aryl α-amino epoxides has been demonstrated. The reaction likely proceeds via the highly strained cyclic nitrogen ylide intermediates generated from aziridines and arynes.

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Roy T, Thangaraj M, Gonnade RG, et al. Synthesis of functionalized amino epoxides by a three-component coupling involving aziridines, arynes and aldehydes. Chem Commun (Camb). 2016;52(58):9044-7doi: 10.1039/c6cc00057f.
Roy, T., Thangaraj, M., Gonnade, R. G., & Biju, A. T. (2016). Synthesis of functionalized amino epoxides by a three-component coupling involving aziridines, arynes and aldehydes. Chemical communications (Cambridge, England), 52(58), 9044-7. https://doi.org/10.1039/c6cc00057f
Roy, Tony, et al. "Synthesis of functionalized amino epoxides by a three-component coupling involving aziridines, arynes and aldehydes." Chemical communications (Cambridge, England) vol. 52,58 (2016): 9044-7. doi: https://doi.org/10.1039/c6cc00057f
Roy T, Thangaraj M, Gonnade RG, Biju AT. Synthesis of functionalized amino epoxides by a three-component coupling involving aziridines, arynes and aldehydes. Chem Commun (Camb). 2016 Jul 12;52(58):9044-7. doi: 10.1039/c6cc00057f. PMID: 27400886.
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Asymmetric synthesis of trisubstituted aziridines via aza-Darzens reaction of chiral sulfinimines.

Organic letters

Moragas T, Churcher I, Lewis W, Stockman RA.
PMID: 25479333
Org Lett. 2014 Dec 19;16(24):6290-3. doi: 10.1021/ol502967x. Epub 2014 Dec 05.

The aza-Darzens reaction of substituted 2-bromoesters with chiral tert-butane- and mesitylsulfinimines provides a rapid access to a range of highly substituted aziridines in good yields and excellent levels of stereoselectivity. The synthetic potential of this protocol is further enhanced...

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Moragas T, Churcher I, Lewis W, et al. Asymmetric synthesis of trisubstituted aziridines via aza-Darzens reaction of chiral sulfinimines. Org Lett. 2014;16(24):6290-3doi: 10.1021/ol502967x.
Moragas, T., Churcher, I., Lewis, W., & Stockman, R. A. (2014). Asymmetric synthesis of trisubstituted aziridines via aza-Darzens reaction of chiral sulfinimines. Organic letters, 16(24), 6290-3. https://doi.org/10.1021/ol502967x
Moragas, Toni, et al. "Asymmetric synthesis of trisubstituted aziridines via aza-Darzens reaction of chiral sulfinimines." Organic letters vol. 16,24 (2014): 6290-3. doi: https://doi.org/10.1021/ol502967x
Moragas T, Churcher I, Lewis W, Stockman RA. Asymmetric synthesis of trisubstituted aziridines via aza-Darzens reaction of chiral sulfinimines. Org Lett. 2014 Dec 19;16(24):6290-3. doi: 10.1021/ol502967x. Epub 2014 Dec 05. PMID: 25479333.
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Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

Beilstein journal of organic chemistry

Jarvis AN, McLaren AB, Osborn HM, Sweeney J.
PMID: 23766800
Beilstein J Org Chem. 2013 May 02;9:852-9. doi: 10.3762/bjoc.9.98. Print 2013.

Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with α-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally...

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Jarvis AN, McLaren AB, Osborn HM, et al. Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines. Beilstein J Org Chem. 2013;9:852-9doi: 10.3762/bjoc.9.98.
Jarvis, A. N., McLaren, A. B., Osborn, H. M., & Sweeney, J. (2013). Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines. Beilstein journal of organic chemistry, 9852-9. https://doi.org/10.3762/bjoc.9.98
Jarvis, Ashley N, et al. "Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines." Beilstein journal of organic chemistry vol. 9 (2013): 852-9. doi: https://doi.org/10.3762/bjoc.9.98
Jarvis AN, McLaren AB, Osborn HM, Sweeney J. Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines. Beilstein J Org Chem. 2013 May 02;9:852-9. doi: 10.3762/bjoc.9.98. Print 2013. PMID: 23766800; PMCID: PMC3678660.
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Sequential Annulation Domino Reaction of Sulfur Ylides and α,β-Unsaturated Cyclic Ketimines: Synthesis of Cyclic 2-Alkenyl Aziridines.

Organic letters

Jia P, Huang Y.
PMID: 27171382
Org Lett. 2016 May 20;18(10):2475-8. doi: 10.1021/acs.orglett.6b01045. Epub 2016 May 12.

A sequential annulation domino reaction of sulfur ylides and α,β-unsaturated cyclic ketimines for the construction of cyclic 2-alkenyl aziridines has been developed. Readily accessible starting materials, a one-pot procedure, excellent functional group compatibility, and mild conditions make this transformation...

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Jia P, Huang Y. Sequential Annulation Domino Reaction of Sulfur Ylides and α,β-Unsaturated Cyclic Ketimines: Synthesis of Cyclic 2-Alkenyl Aziridines. Org Lett. 2016;18(10):2475-8doi: 10.1021/acs.orglett.6b01045.
Jia, P., & Huang, Y. (2016). Sequential Annulation Domino Reaction of Sulfur Ylides and α,β-Unsaturated Cyclic Ketimines: Synthesis of Cyclic 2-Alkenyl Aziridines. Organic letters, 18(10), 2475-8. https://doi.org/10.1021/acs.orglett.6b01045
Jia, Penghao, and Huang, You. "Sequential Annulation Domino Reaction of Sulfur Ylides and α,β-Unsaturated Cyclic Ketimines: Synthesis of Cyclic 2-Alkenyl Aziridines." Organic letters vol. 18,10 (2016): 2475-8. doi: https://doi.org/10.1021/acs.orglett.6b01045
Jia P, Huang Y. Sequential Annulation Domino Reaction of Sulfur Ylides and α,β-Unsaturated Cyclic Ketimines: Synthesis of Cyclic 2-Alkenyl Aziridines. Org Lett. 2016 May 20;18(10):2475-8. doi: 10.1021/acs.orglett.6b01045. Epub 2016 May 12. PMID: 27171382.
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Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines.

Organic letters

Lin TY, Wu HH, Feng JJ, Zhang J.
PMID: 28530815
Org Lett. 2017 Jun 02;19(11):2897-2900. doi: 10.1021/acs.orglett.7b01136. Epub 2017 May 22.

By taking advantage of chirality-transfer strategy, a chemo- and regioselective allylic alkylation of naphthols and phenols with vinylaziridines provides an atom-economic and efficient method for the synthesis of enantioenriched 2-vinyl-2-arylethylamine derivatives. Use of readily available starting materials, a broad...

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Lin TY, Wu HH, Feng JJ, et al. Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines. Org Lett. 2017;19(11):2897-2900doi: 10.1021/acs.orglett.7b01136.
Lin, T. Y., Wu, H. H., Feng, J. J., & Zhang, J. (2017). Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines. Organic letters, 19(11), 2897-2900. https://doi.org/10.1021/acs.orglett.7b01136
Lin, Tao-Yan, et al. "Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines." Organic letters vol. 19,11 (2017): 2897-2900. doi: https://doi.org/10.1021/acs.orglett.7b01136
Lin TY, Wu HH, Feng JJ, Zhang J. Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines. Org Lett. 2017 Jun 02;19(11):2897-2900. doi: 10.1021/acs.orglett.7b01136. Epub 2017 May 22. PMID: 28530815.
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Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Feraldi-Xypolia A, Gomez Pardo D, Cossy J.
PMID: 26218227
Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23.

A ring contraction of 3-hydroxy-3-(trifluoromethyl)piperidines was achieved via an aziridinium intermediate. This contraction facilitates the synthesis of a series of 2-substituted 2-(trifluoromethyl)pyrrolidines incorporating a quaternary center at the C2 position.

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Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015;21(37):12876-80doi: 10.1002/chem.201502084.
Feraldi-Xypolia, A., Gomez Pardo, D., & Cossy, J. (2015). Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry (Weinheim an der Bergstrasse, Germany), 21(37), 12876-80. https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia, Alexandra, et al. "Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,37 (2015): 12876-80. doi: https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23. PMID: 26218227.
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Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride.

ChemistryOpen

Schjoeth-Eskesen C, Hansen PR, Kjaer A, Gillings N.
PMID: 25861572
ChemistryOpen. 2015 Feb;4(1):65-71. doi: 10.1002/open.201402081. Epub 2014 Nov 21.

Aziridines can undergo a range of ring-opening reactions with nucleophiles. The regio- and stereochemistry of the products depend on the substituents on the aziridine. Aziridine ring-opening reactions have rarely been used in radiosynthesis. Herein we report the ring opening...

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Schjoeth-Eskesen C, Hansen PR, Kjaer A, et al. Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride. ChemistryOpen. 2014;4(1):65-71doi: 10.1002/open.201402081.
Schjoeth-Eskesen, C., Hansen, P. R., Kjaer, A., & Gillings, N. (2015). Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride. ChemistryOpen, 4(1), 65-71. https://doi.org/10.1002/open.201402081
Schjoeth-Eskesen, Christina, et al. "Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride." ChemistryOpen vol. 4,1 (2015): 65-71. doi: https://doi.org/10.1002/open.201402081
Schjoeth-Eskesen C, Hansen PR, Kjaer A, Gillings N. Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride. ChemistryOpen. 2015 Feb;4(1):65-71. doi: 10.1002/open.201402081. Epub 2014 Nov 21. PMID: 25861572; PMCID: PMC4380955.
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Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange.

Organic letters

Boultwood T, Bull JA.
PMID: 24786465
Org Lett. 2014 May 16;16(10):2740-3. doi: 10.1021/ol501024y. Epub 2014 May 01.

Lithium-iodine exchange on alkyl- or aryl-substituted N-tosyliodoaziridines afforded unstabilized aziridinyllithiums, which were subsequently trapped at low temperatures with a range of carbon and heteroatom electrophiles affording cis-substituted aziridines exclusively. When using isocyanates as electrophiles, access to aziridine carboxamides or...

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Boultwood T, Bull JA. Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange. Org Lett. 2014;16(10):2740-3doi: 10.1021/ol501024y.
Boultwood, T., & Bull, J. A. (2014). Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange. Organic letters, 16(10), 2740-3. https://doi.org/10.1021/ol501024y
Boultwood, Tom, and Bull, James A. "Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange." Organic letters vol. 16,10 (2014): 2740-3. doi: https://doi.org/10.1021/ol501024y
Boultwood T, Bull JA. Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange. Org Lett. 2014 May 16;16(10):2740-3. doi: 10.1021/ol501024y. Epub 2014 May 01. PMID: 24786465.
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Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines.

The Journal of organic chemistry

Dejaegher Y, Mangelinckx S, De Kimpe N.
PMID: 11925211
J Org Chem. 2002 Apr 05;67(7):2075-81. doi: 10.1021/jo010914j.

An easy synthesis of 2-aryl-3,3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3,3-dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2 + 2] cycloaddition....

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Dejaegher Y, Mangelinckx S, De Kimpe N. Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines. J Org Chem. 2002;67(7):2075-81doi: 10.1021/jo010914j.
Dejaegher, Y., Mangelinckx, S., & De Kimpe, N. (2002). Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines. The Journal of organic chemistry, 67(7), 2075-81. https://doi.org/10.1021/jo010914j
Dejaegher, Yves, et al. "Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines." The Journal of organic chemistry vol. 67,7 (2002): 2075-81. doi: https://doi.org/10.1021/jo010914j
Dejaegher Y, Mangelinckx S, De Kimpe N. Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines. J Org Chem. 2002 Apr 05;67(7):2075-81. doi: 10.1021/jo010914j. PMID: 11925211.
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