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Chiral cyclopentadienyl iridium(III) complexes promote enantioselective cycloisomerizations giving fused cyclopropanes.

Angewandte Chemie (International ed. in English)

Dieckmann M, Jang YS, Cramer N.
PMID: 26310394
Angew Chem Int Ed Engl. 2015 Oct 05;54(41):12149-52. doi: 10.1002/anie.201506483. Epub 2015 Aug 27.

The cyclopentadienyl (Cp) group is a very important ligand for many transition-metal complexes which have been applied in catalysis. The availability of chiral cyclopentadienyl ligands (Cp(x) ) lags behind other ligand classes, thus hampering the investigation of enantioselective processes....

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Dieckmann M, Jang YS, Cramer N. Chiral cyclopentadienyl iridium(III) complexes promote enantioselective cycloisomerizations giving fused cyclopropanes. Angew Chem Int Ed Engl. 2015;54(41):12149-52doi: 10.1002/anie.201506483.
Dieckmann, M., Jang, Y. S., & Cramer, N. (2015). Chiral cyclopentadienyl iridium(III) complexes promote enantioselective cycloisomerizations giving fused cyclopropanes. Angewandte Chemie (International ed. in English), 54(41), 12149-52. https://doi.org/10.1002/anie.201506483
Dieckmann, Michael, et al. "Chiral cyclopentadienyl iridium(III) complexes promote enantioselective cycloisomerizations giving fused cyclopropanes." Angewandte Chemie (International ed. in English) vol. 54,41 (2015): 12149-52. doi: https://doi.org/10.1002/anie.201506483
Dieckmann M, Jang YS, Cramer N. Chiral cyclopentadienyl iridium(III) complexes promote enantioselective cycloisomerizations giving fused cyclopropanes. Angew Chem Int Ed Engl. 2015 Oct 05;54(41):12149-52. doi: 10.1002/anie.201506483. Epub 2015 Aug 27. PMID: 26310394.
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Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes.

Journal of the American Chemical Society

Müller DS, Marek I.
PMID: 26624801
J Am Chem Soc. 2015 Dec 16;137(49):15414-7. doi: 10.1021/jacs.5b11220. Epub 2015 Dec 01.

The enantioselective synthesis of cyclopropylzinc reagents has been achieved via a copper-catalyzed carbozincation of 3,3-disubstituted cyclopropenes with diorganozinc reagents. The obtained organozinc compounds can be easily functionalized with a broad range of electrophiles, including palladium-catalyzed cross-couplings, affording highly substituted...

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Müller DS, Marek I. Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes. J Am Chem Soc. 2015;137(49):15414-7doi: 10.1021/jacs.5b11220.
Müller, D. S., & Marek, I. (2015). Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes. Journal of the American Chemical Society, 137(49), 15414-7. https://doi.org/10.1021/jacs.5b11220
Müller, Daniel S, and Marek, Ilan. "Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes." Journal of the American Chemical Society vol. 137,49 (2015): 15414-7. doi: https://doi.org/10.1021/jacs.5b11220
Müller DS, Marek I. Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes. J Am Chem Soc. 2015 Dec 16;137(49):15414-7. doi: 10.1021/jacs.5b11220. Epub 2015 Dec 01. PMID: 26624801.
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Dialkyl Phosphite-Initiated Cyclopropanation of α,β-Unsaturated Ketones Using α-Ketoesters or Isatin Derivatives.

The Journal of organic chemistry

Yin D, Liu H, Lu CD, Xu YJ.
PMID: 28221041
J Org Chem. 2017 Mar 17;82(6):3252-3261. doi: 10.1021/acs.joc.6b03009. Epub 2017 Mar 02.

Efficient cyclopropanation of α,β-unsaturated ketones using α-ketoesters or isatin derivatives is reported. The cyclopropanation reaction occurs via a cascade transformation that starts with addition of deprotonated dialkyl phosphite to the keto groups of α-ketoesters or isatin derivatives, followed by...

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Yin D, Liu H, Lu CD, et al. Dialkyl Phosphite-Initiated Cyclopropanation of α,β-Unsaturated Ketones Using α-Ketoesters or Isatin Derivatives. J Org Chem. 2017;82(6):3252-3261doi: 10.1021/acs.joc.6b03009.
Yin, D., Liu, H., Lu, C. D., & Xu, Y. J. (2017). Dialkyl Phosphite-Initiated Cyclopropanation of α,β-Unsaturated Ketones Using α-Ketoesters or Isatin Derivatives. The Journal of organic chemistry, 82(6), 3252-3261. https://doi.org/10.1021/acs.joc.6b03009
Yin, Deng, et al. "Dialkyl Phosphite-Initiated Cyclopropanation of α,β-Unsaturated Ketones Using α-Ketoesters or Isatin Derivatives." The Journal of organic chemistry vol. 82,6 (2017): 3252-3261. doi: https://doi.org/10.1021/acs.joc.6b03009
Yin D, Liu H, Lu CD, Xu YJ. Dialkyl Phosphite-Initiated Cyclopropanation of α,β-Unsaturated Ketones Using α-Ketoesters or Isatin Derivatives. J Org Chem. 2017 Mar 17;82(6):3252-3261. doi: 10.1021/acs.joc.6b03009. Epub 2017 Mar 02. PMID: 28221041.
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Rhodium-catalyzed cyclopropanation of fluorinated olefins: a straightforward route to highly functionalized fluorocyclopropanes.

Organic letters

Pons A, Beucher H, Ivashkin P, Lemonnier G, Poisson T, Charette AB, Jubault P, Pannecoucke X.
PMID: 25768041
Org Lett. 2015 Apr 03;17(7):1790-3. doi: 10.1021/acs.orglett.5b00576. Epub 2015 Mar 13.

An efficient access to highly functionalized monofluorocyclopropanes is described. The developed methodology allowed straightforward access to a large panel of polysubstituted fluorinated cyclopropanes in good to excellent yields and good diastereoselectivities. The Rh-catalyzed cyclopropanation proved to be efficient on...

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Pons A, Beucher H, Ivashkin P, et al. Rhodium-catalyzed cyclopropanation of fluorinated olefins: a straightforward route to highly functionalized fluorocyclopropanes. Org Lett. 2015;17(7):1790-3doi: 10.1021/acs.orglett.5b00576.
Pons, A., Beucher, H., Ivashkin, P., Lemonnier, G., Poisson, T., Charette, A. B., Jubault, P., & Pannecoucke, X. (2015). Rhodium-catalyzed cyclopropanation of fluorinated olefins: a straightforward route to highly functionalized fluorocyclopropanes. Organic letters, 17(7), 1790-3. https://doi.org/10.1021/acs.orglett.5b00576
Pons, Amandine, et al. "Rhodium-catalyzed cyclopropanation of fluorinated olefins: a straightforward route to highly functionalized fluorocyclopropanes." Organic letters vol. 17,7 (2015): 1790-3. doi: https://doi.org/10.1021/acs.orglett.5b00576
Pons A, Beucher H, Ivashkin P, Lemonnier G, Poisson T, Charette AB, Jubault P, Pannecoucke X. Rhodium-catalyzed cyclopropanation of fluorinated olefins: a straightforward route to highly functionalized fluorocyclopropanes. Org Lett. 2015 Apr 03;17(7):1790-3. doi: 10.1021/acs.orglett.5b00576. Epub 2015 Mar 13. PMID: 25768041.
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Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes.

Angewandte Chemie (International ed. in English)

Li M, Kwong FY.
PMID: 29517160
Angew Chem Int Ed Engl. 2018 May 28;57(22):6512-6516. doi: 10.1002/anie.201801706. Epub 2018 Apr 14.

A cobalt-catalyzed chelation-assisted tandem C-H activation/C-C cleavage/C-H cyclization of aromatic amides with alkylidenecyclopropanes is reported. This process allows the sequential formation of two C-C bonds, which is in sharp contrast to previous reports on using rhodium catalysts for the...

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Li M, Kwong FY. Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes. Angew Chem Int Ed Engl. 2018;57(22):6512-6516doi: 10.1002/anie.201801706.
Li, M., & Kwong, F. Y. (2018). Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes. Angewandte Chemie (International ed. in English), 57(22), 6512-6516. https://doi.org/10.1002/anie.201801706
Li, Mingliang, and Kwong, Fuk Yee. "Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes." Angewandte Chemie (International ed. in English) vol. 57,22 (2018): 6512-6516. doi: https://doi.org/10.1002/anie.201801706
Li M, Kwong FY. Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes. Angew Chem Int Ed Engl. 2018 May 28;57(22):6512-6516. doi: 10.1002/anie.201801706. Epub 2018 Apr 14. PMID: 29517160.
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Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate.

Journal of the American Chemical Society

Pitts CR, Ling B, Snyder JA, Bragg AE, Lectka T.
PMID: 27136383
J Am Chem Soc. 2016 May 25;138(20):6598-609. doi: 10.1021/jacs.6b02838. Epub 2016 May 16.

We have discovered a highly regioselective aminofluorination of cyclopropanes. Remarkably, four unique sets of conditions-two photochemical, two purely chemical-generated the same aminofluorinated adducts in good to excellent yields. The multiple, diverse ways in which the reaction could be initiated...

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Pitts CR, Ling B, Snyder JA, et al. Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate. J Am Chem Soc. 2016;138(20):6598-609doi: 10.1021/jacs.6b02838.
Pitts, C. R., Ling, B., Snyder, J. A., Bragg, A. E., & Lectka, T. (2016). Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate. Journal of the American Chemical Society, 138(20), 6598-609. https://doi.org/10.1021/jacs.6b02838
Pitts, Cody Ross, et al. "Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate." Journal of the American Chemical Society vol. 138,20 (2016): 6598-609. doi: https://doi.org/10.1021/jacs.6b02838
Pitts CR, Ling B, Snyder JA, Bragg AE, Lectka T. Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate. J Am Chem Soc. 2016 May 25;138(20):6598-609. doi: 10.1021/jacs.6b02838. Epub 2016 May 16. PMID: 27136383.
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Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde.

Organic & biomolecular chemistry

Fu X, Lin L, Xia Y, Zhou P, Liu X, Feng X.
PMID: 27220905
Org Biomol Chem. 2016 Jul 07;14(25):5914-7. doi: 10.1039/c6ob00948d. Epub 2016 May 25.

A highly diastereo- and enantioselective [3 + 3] annulation of donor-acceptor cyclopropanes with mercaptoacetaldehyde has been developed. In the presence of a N,N'-dioxide-Sc(iii) complex as the catalyst, a number of aromatic substituted cyclopropyl ketones reacted with mercaptoacetaldehyde smoothly, providing...

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Fu X, Lin L, Xia Y, et al. Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde. Org Biomol Chem. 2016;14(25):5914-7doi: 10.1039/c6ob00948d.
Fu, X., Lin, L., Xia, Y., Zhou, P., Liu, X., & Feng, X. (2016). Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde. Organic & biomolecular chemistry, 14(25), 5914-7. https://doi.org/10.1039/c6ob00948d
Fu, Xuan, et al. "Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde." Organic & biomolecular chemistry vol. 14,25 (2016): 5914-7. doi: https://doi.org/10.1039/c6ob00948d
Fu X, Lin L, Xia Y, Zhou P, Liu X, Feng X. Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde. Org Biomol Chem. 2016 Jul 07;14(25):5914-7. doi: 10.1039/c6ob00948d. Epub 2016 May 25. PMID: 27220905.
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Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation.

The Journal of organic chemistry

Joshi-Pangu A, Cohen RD, Tudge MT, Chen Y.
PMID: 27021027
J Org Chem. 2016 Apr 15;81(8):3070-5. doi: 10.1021/acs.joc.6b00322. Epub 2016 Apr 06.

The dearomatization of a series of electron-deficient nitrogen heterocycles has been achieved through a cobalt-catalyzed asymmetric cyclopropanation reaction. This reaction proceeds with high levels of enantio- and diastereoselectivity to afford unique cyclopropanes that can be further functionalized to provide...

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Joshi-Pangu A, Cohen RD, Tudge MT, et al. Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation. J Org Chem. 2016;81(8):3070-5doi: 10.1021/acs.joc.6b00322.
Joshi-Pangu, A., Cohen, R. D., Tudge, M. T., & Chen, Y. (2016). Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation. The Journal of organic chemistry, 81(8), 3070-5. https://doi.org/10.1021/acs.joc.6b00322
Joshi-Pangu, Amruta, et al. "Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation." The Journal of organic chemistry vol. 81,8 (2016): 3070-5. doi: https://doi.org/10.1021/acs.joc.6b00322
Joshi-Pangu A, Cohen RD, Tudge MT, Chen Y. Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation. J Org Chem. 2016 Apr 15;81(8):3070-5. doi: 10.1021/acs.joc.6b00322. Epub 2016 Apr 06. PMID: 27021027.
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Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles.

Organic & biomolecular chemistry

Liu RR, Ye SC, Lu CJ, Xiang B, Gao J, Jia YX.
PMID: 25832795
Org Biomol Chem. 2015 May 07;13(17):4855-8. doi: 10.1039/c5ob00523j.

A novel method for the C-C bond cleavage of cyclopropanes was developed by gold-catalyzed cycloisomerization of 2-(1-alkynyl-cyclopropyl)pyridine with nucleophiles, which provides efficient access to structurally diverse indolizines under mild conditions. A series of N-, C- and O-based nucleophiles were...

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Liu RR, Ye SC, Lu CJ, et al. Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles. Org Biomol Chem. 2015;13(17):4855-8doi: 10.1039/c5ob00523j.
Liu, R. R., Ye, S. C., Lu, C. J., Xiang, B., Gao, J., & Jia, Y. X. (2015). Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles. Organic & biomolecular chemistry, 13(17), 4855-8. https://doi.org/10.1039/c5ob00523j
Liu, Ren-Rong, et al. "Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles." Organic & biomolecular chemistry vol. 13,17 (2015): 4855-8. doi: https://doi.org/10.1039/c5ob00523j
Liu RR, Ye SC, Lu CJ, Xiang B, Gao J, Jia YX. Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles. Org Biomol Chem. 2015 May 07;13(17):4855-8. doi: 10.1039/c5ob00523j. PMID: 25832795.
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Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes.

Organic letters

Rösner C, Hennecke U.
PMID: 26101939
Org Lett. 2015 Jul 02;17(13):3226-9. doi: 10.1021/acs.orglett.5b01315. Epub 2015 Jun 23.

An efficient method for the halocyclization of cyclopropanes has been developed. The cyclopropanes undergo a 1,3-addition reaction to form homohalocyclization products compared to conventional alkene halocyclizations. The reaction can be induced by various electrophilic halogenating agents including 1,3-dibromo-5,5-dimethylhydantoin and...

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Rösner C, Hennecke U. Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes. Org Lett. 2015;17(13):3226-9doi: 10.1021/acs.orglett.5b01315.
Rösner, C., & Hennecke, U. (2015). Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes. Organic letters, 17(13), 3226-9. https://doi.org/10.1021/acs.orglett.5b01315
Rösner, Christian, and Hennecke, Ulrich. "Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes." Organic letters vol. 17,13 (2015): 3226-9. doi: https://doi.org/10.1021/acs.orglett.5b01315
Rösner C, Hennecke U. Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes. Org Lett. 2015 Jul 02;17(13):3226-9. doi: 10.1021/acs.orglett.5b01315. Epub 2015 Jun 23. PMID: 26101939.
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Reactions of Donor-Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert.

Angewandte Chemie (International ed. in English)

Lücht A, Patalag LJ, Augustin AU, Jones PG, Werz DB.
PMID: 28654714
Angew Chem Int Ed Engl. 2017 Aug 21;56(35):10587-10591. doi: 10.1002/anie.201703732. Epub 2017 Jul 19.

Reactions of 2-arylcyclopropane dicarboxylates with naphthoquinones are reported. The key feature was the use of catalytic amounts of SnCl

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Lücht A, Patalag LJ, Augustin AU, et al. Reactions of Donor-Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert. Angew Chem Int Ed Engl. 2017;56(35):10587-10591doi: 10.1002/anie.201703732.
Lücht, A., Patalag, L. J., Augustin, A. U., Jones, P. G., & Werz, D. B. (2017). Reactions of Donor-Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert. Angewandte Chemie (International ed. in English), 56(35), 10587-10591. https://doi.org/10.1002/anie.201703732
Lücht, Alexander, et al. "Reactions of Donor-Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert." Angewandte Chemie (International ed. in English) vol. 56,35 (2017): 10587-10591. doi: https://doi.org/10.1002/anie.201703732
Lücht A, Patalag LJ, Augustin AU, Jones PG, Werz DB. Reactions of Donor-Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert. Angew Chem Int Ed Engl. 2017 Aug 21;56(35):10587-10591. doi: 10.1002/anie.201703732. Epub 2017 Jul 19. PMID: 28654714.
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A Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ivanova OA, Budynina EM, Khrustalev VN, Skvortsov DA, Trushkov IV, Melnikov MY.
PMID: 26251074
Chemistry. 2016 Jan 22;22(4):1223-7. doi: 10.1002/chem.201502287. Epub 2015 Aug 06.

A rapid new approach to produce biologically relevant bisindoles, namely indolyltetrahydrocarbazoles and indolo[3,2-b]carbazoles, has been developed, based on the Ga(OTf)3 -catalyzed [3+3] cyclodimerization of indole-derived donor-acceptor cyclopropanes. Chemoselectivity of the process depends on the location of the three-membered ring...

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Ivanova OA, Budynina EM, Khrustalev VN, et al. A Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes. Chemistry. 2015;22(4):1223-7doi: 10.1002/chem.201502287.
Ivanova, O. A., Budynina, E. M., Khrustalev, V. N., Skvortsov, D. A., Trushkov, I. V., & Melnikov, M. Y. (2016). A Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes. Chemistry (Weinheim an der Bergstrasse, Germany), 22(4), 1223-7. https://doi.org/10.1002/chem.201502287
Ivanova, Olga A, et al. "A Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,4 (2016): 1223-7. doi: https://doi.org/10.1002/chem.201502287
Ivanova OA, Budynina EM, Khrustalev VN, Skvortsov DA, Trushkov IV, Melnikov MY. A Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes. Chemistry. 2016 Jan 22;22(4):1223-7. doi: 10.1002/chem.201502287. Epub 2015 Aug 06. PMID: 26251074.
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