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Palladium(II)-Catalyzed 1,4-Oxidation of 2-Aryl-1,3-cyclohexadienes. Application to the Synthesis of (+/-)-Epibatidine and Analogues.

The Journal of organic chemistry

Palmgren A, Larsson AL, Bäckvall JE, Helquist P.
PMID: 11674155
J Org Chem. 1999 Feb 05;64(3):836-842. doi: 10.1021/jo981668n.

Palladium(II)-catalyzed 1,4-chloroacetoxylation of 2-aryl-1,3-cyclohexadienes 2a and 2b resulted in a highly regio- and stereoselective reaction to give cis-1-acetoxy-3-aryl-4-chloro-2-cyclohexenes 7a and 7b, respectively. The phenyl adduct 7a was subjected to the synthesis of exo- and endo-2-phenyl-7-azabicyclo[2.2.1]heptanes (exo-1a and endo-1a). Stereoselective...

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Palmgren A, Larsson AL, Bäckvall JE, et al. Palladium(II)-Catalyzed 1,4-Oxidation of 2-Aryl-1,3-cyclohexadienes. Application to the Synthesis of (+/-)-Epibatidine and Analogues. J Org Chem. 1999;64(3):836-842doi: 10.1021/jo981668n.
Palmgren, A., Larsson, A. L., Bäckvall, J. E., & Helquist, P. (1999). Palladium(II)-Catalyzed 1,4-Oxidation of 2-Aryl-1,3-cyclohexadienes. Application to the Synthesis of (+/-)-Epibatidine and Analogues. The Journal of organic chemistry, 64(3), 836-842. https://doi.org/10.1021/jo981668n
Palmgren, Andreas, et al. "Palladium(II)-Catalyzed 1,4-Oxidation of 2-Aryl-1,3-cyclohexadienes. Application to the Synthesis of (+/-)-Epibatidine and Analogues." The Journal of organic chemistry vol. 64,3 (1999): 836-842. doi: https://doi.org/10.1021/jo981668n
Palmgren A, Larsson AL, Bäckvall JE, Helquist P. Palladium(II)-Catalyzed 1,4-Oxidation of 2-Aryl-1,3-cyclohexadienes. Application to the Synthesis of (+/-)-Epibatidine and Analogues. J Org Chem. 1999 Feb 05;64(3):836-842. doi: 10.1021/jo981668n. PMID: 11674155.
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"Dimers" and "trimers" of tetrahydroindenes and hexahydroazulenes, respectively generated from [2-(1-cycloalkenyl)ethynyl]carbene complexes (M = W, Cr) by cascade cyclization/cycloaddition reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Wu HP, Aumann R, Fröhlich R, Saarenketo P.
PMID: 11261668
Chemistry. 2001 Feb 02;7(3):700-10. doi: 10.1002/1521-3765(20010202)7:3<700::aid-chem700>3.0.co;2-d.

A cascade of cyclization/cycloaddition reactions was triggered by addition of protic oxygen nucleophiles ROH 2 (RO = CH3CO2, PhCO2, PhO) to [2-(1-cyclohexenyl)ethynyl]carbene complexes 1b and 1c (M=W, Cr, respectively), affording highly strained "dimers" 11/11' and "trimers" 12 of the...

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Wu HP, Aumann R, Fröhlich R, et al. "Dimers" and "trimers" of tetrahydroindenes and hexahydroazulenes, respectively generated from [2-(1-cycloalkenyl)ethynyl]carbene complexes (M = W, Cr) by cascade cyclization/cycloaddition reactions. Chemistry. 2001;7(3):700-10doi: 10.1002/1521-3765(20010202)7:3<700::aid-chem700>3.0.co;2-d.
Wu, H. P., Aumann, R., Fröhlich, R., & Saarenketo, P. (2001). "Dimers" and "trimers" of tetrahydroindenes and hexahydroazulenes, respectively generated from [2-(1-cycloalkenyl)ethynyl]carbene complexes (M = W, Cr) by cascade cyclization/cycloaddition reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 7(3), 700-10. https://doi.org/10.1002/1521-3765(20010202)7:3<700::aid-chem700>3.0.co;2-d
Wu, H P, et al. ""Dimers" and "trimers" of tetrahydroindenes and hexahydroazulenes, respectively generated from [2-(1-cycloalkenyl)ethynyl]carbene complexes (M = W, Cr) by cascade cyclization/cycloaddition reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 7,3 (2001): 700-10. doi: https://doi.org/10.1002/1521-3765(20010202)7:3<700::aid-chem700>3.0.co;2-d
Wu HP, Aumann R, Fröhlich R, Saarenketo P. "Dimers" and "trimers" of tetrahydroindenes and hexahydroazulenes, respectively generated from [2-(1-cycloalkenyl)ethynyl]carbene complexes (M = W, Cr) by cascade cyclization/cycloaddition reactions. Chemistry. 2001 Feb 02;7(3):700-10. doi: 10.1002/1521-3765(20010202)7:3<700::aid-chem700>3.0.co;2-d. PMID: 11261668.
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Ketone-catalyzed asymmetric epoxidation reactions.

Accounts of chemical research

Yang D.
PMID: 15311948
Acc Chem Res. 2004 Aug;37(8):497-505. doi: 10.1021/ar030065h.

This Account summarizes our efforts in developing organic ketone catalysts for enantioselective and diastereoselective epoxidation of olefins. We have developed an efficient and general protocol for epoxidation of olefins using dioxiranes generated in situ from activated ketones and Oxone...

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Yang D. Ketone-catalyzed asymmetric epoxidation reactions. Acc Chem Res. 2004;37(8):497-505doi: 10.1021/ar030065h.
Yang, D. (2004). Ketone-catalyzed asymmetric epoxidation reactions. Accounts of chemical research, 37(8), 497-505. https://doi.org/10.1021/ar030065h
Yang, Dan. "Ketone-catalyzed asymmetric epoxidation reactions." Accounts of chemical research vol. 37,8 (2004): 497-505. doi: https://doi.org/10.1021/ar030065h
Yang D. Ketone-catalyzed asymmetric epoxidation reactions. Acc Chem Res. 2004 Aug;37(8):497-505. doi: 10.1021/ar030065h. PMID: 15311948.
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Three-component reactions with (S)-methyl pyroglutamate: an efficient way to diversely substituted asymmetric amidocyclohexenes.

Chemistry, an Asian journal

Hübner S, Michalik D, Jiao H, Neumann H, Klaus S, Strübing D, Spannenberg A, Beller M.
PMID: 17492706
Chem Asian J. 2007 Jun 04;2(6):734-46. doi: 10.1002/asia.200700031.

Chiral N-dienyl lactams are crucial building blocks for the synthesis of complex organic compounds. However, their generation is rather challenging. This paper reports the novel one-pot reaction of (S)-methyl pyroglutamate as the amide component with different aldehydes and dienophiles...

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Hübner S, Michalik D, Jiao H, et al. Three-component reactions with (S)-methyl pyroglutamate: an efficient way to diversely substituted asymmetric amidocyclohexenes. Chem Asian J. 2007;2(6):734-46doi: 10.1002/asia.200700031.
Hübner, S., Michalik, D., Jiao, H., Neumann, H., Klaus, S., Strübing, D., Spannenberg, A., & Beller, M. (2007). Three-component reactions with (S)-methyl pyroglutamate: an efficient way to diversely substituted asymmetric amidocyclohexenes. Chemistry, an Asian journal, 2(6), 734-46. https://doi.org/10.1002/asia.200700031
Hübner, Sandra, et al. "Three-component reactions with (S)-methyl pyroglutamate: an efficient way to diversely substituted asymmetric amidocyclohexenes." Chemistry, an Asian journal vol. 2,6 (2007): 734-46. doi: https://doi.org/10.1002/asia.200700031
Hübner S, Michalik D, Jiao H, Neumann H, Klaus S, Strübing D, Spannenberg A, Beller M. Three-component reactions with (S)-methyl pyroglutamate: an efficient way to diversely substituted asymmetric amidocyclohexenes. Chem Asian J. 2007 Jun 04;2(6):734-46. doi: 10.1002/asia.200700031. PMID: 17492706.
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A QSPR model for the prediction of the "fish-tail" temperature of C(i)E4/water/polar hydrocarbon oil systems.

Langmuir : the ACS journal of surfaces and colloids

Bouton F, Durand M, Nardello-Rataj V, Borosy AP, Quellet C, Aubry JM.
PMID: 20459074
Langmuir. 2010 Jun 01;26(11):7962-70. doi: 10.1021/la904836m.

The fish-tail temperatures denoted as T* have been determined or collected for 85 ternary systems based on three tetraethylene glycol monoalkyl ethers C(i)E(4) (i = 6, 8, 10), water, and 43 hydrocarbon oils of various hydrophobicities. Fourteen fragrant mono-...

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Bouton F, Durand M, Nardello-Rataj V, et al. A QSPR model for the prediction of the "fish-tail" temperature of C(i)E4/water/polar hydrocarbon oil systems. Langmuir. 2010;26(11):7962-70doi: 10.1021/la904836m.
Bouton, F., Durand, M., Nardello-Rataj, V., Borosy, A. P., Quellet, C., & Aubry, J. M. (2010). A QSPR model for the prediction of the "fish-tail" temperature of C(i)E4/water/polar hydrocarbon oil systems. Langmuir : the ACS journal of surfaces and colloids, 26(11), 7962-70. https://doi.org/10.1021/la904836m
Bouton, François, et al. "A QSPR model for the prediction of the "fish-tail" temperature of C(i)E4/water/polar hydrocarbon oil systems." Langmuir : the ACS journal of surfaces and colloids vol. 26,11 (2010): 7962-70. doi: https://doi.org/10.1021/la904836m
Bouton F, Durand M, Nardello-Rataj V, Borosy AP, Quellet C, Aubry JM. A QSPR model for the prediction of the "fish-tail" temperature of C(i)E4/water/polar hydrocarbon oil systems. Langmuir. 2010 Jun 01;26(11):7962-70. doi: 10.1021/la904836m. PMID: 20459074.
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Mechanisms of the InCl3-catalyzed type-I, II, and III cycloisomerizations of 1,6-enynes.

The Journal of organic chemistry

Zhuo LG, Zhang JJ, Yu ZX.
PMID: 24665901
J Org Chem. 2014 May 02;79(9):3809-20. doi: 10.1021/jo500059j. Epub 2014 Apr 15.

InCl3-catalyzed cycloisomerizations of 1,6-enynes can give either type-I dienes and cyclohexenes (type-III dienes), or type-II dienes, depending on the substitutions in the substrates. Previously, we studied how the type-II diene products were generated and found that the real catalytic...

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Zhuo LG, Zhang JJ, Yu ZX. Mechanisms of the InCl3-catalyzed type-I, II, and III cycloisomerizations of 1,6-enynes. J Org Chem. 2014;79(9):3809-20doi: 10.1021/jo500059j.
Zhuo, L. G., Zhang, J. J., & Yu, Z. X. (2014). Mechanisms of the InCl3-catalyzed type-I, II, and III cycloisomerizations of 1,6-enynes. The Journal of organic chemistry, 79(9), 3809-20. https://doi.org/10.1021/jo500059j
Zhuo, Lian-Gang, et al. "Mechanisms of the InCl3-catalyzed type-I, II, and III cycloisomerizations of 1,6-enynes." The Journal of organic chemistry vol. 79,9 (2014): 3809-20. doi: https://doi.org/10.1021/jo500059j
Zhuo LG, Zhang JJ, Yu ZX. Mechanisms of the InCl3-catalyzed type-I, II, and III cycloisomerizations of 1,6-enynes. J Org Chem. 2014 May 02;79(9):3809-20. doi: 10.1021/jo500059j. Epub 2014 Apr 15. PMID: 24665901.
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Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations.

Organic letters

Shintani R, Moriya K, Hayashi T.
PMID: 22612531
Org Lett. 2012 Jun 01;14(11):2902-5. doi: 10.1021/ol301191u. Epub 2012 May 21.

A palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with alkynes has been developed to give silicon-stereogenic 1-sila-2-cyclohexenes with high enantioselectivity. The products thus obtained undergo further derivatizations with complete stereoselectivity, and a new catalytic cycle involving alkyne coordination (oxidative cyclization)-transmetalation (σ-bond...

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Shintani R, Moriya K, Hayashi T. Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations. Org Lett. 2012;14(11):2902-5doi: 10.1021/ol301191u.
Shintani, R., Moriya, K., & Hayashi, T. (2012). Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations. Organic letters, 14(11), 2902-5. https://doi.org/10.1021/ol301191u
Shintani, Ryo, et al. "Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations." Organic letters vol. 14,11 (2012): 2902-5. doi: https://doi.org/10.1021/ol301191u
Shintani R, Moriya K, Hayashi T. Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations. Org Lett. 2012 Jun 01;14(11):2902-5. doi: 10.1021/ol301191u. Epub 2012 May 21. PMID: 22612531.
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Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Chen XY, Li S, Liu Q, Kumar M, Peuronen A, Rissanen K, Enders D.
PMID: 29847691
Chemistry. 2018 Jul 11;24(39):9735-9738. doi: 10.1002/chem.201802420. Epub 2018 Jun 25.

A highly efficient strategy for the kinetic resolution of Michael adducts was realized using a chiral N-heterocyclic carbene catalyst. The kinetic resolution provides a new convenient route to single diastereomers of cyclohexenes and Michael adducts in good yields with...

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Chen XY, Li S, Liu Q, et al. Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes. Chemistry. 2018;24(39):9735-9738doi: 10.1002/chem.201802420.
Chen, X. Y., Li, S., Liu, Q., Kumar, M., Peuronen, A., Rissanen, K., & Enders, D. (2018). Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes. Chemistry (Weinheim an der Bergstrasse, Germany), 24(39), 9735-9738. https://doi.org/10.1002/chem.201802420
Chen, Xiang-Yu, et al. "Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,39 (2018): 9735-9738. doi: https://doi.org/10.1002/chem.201802420
Chen XY, Li S, Liu Q, Kumar M, Peuronen A, Rissanen K, Enders D. Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes. Chemistry. 2018 Jul 11;24(39):9735-9738. doi: 10.1002/chem.201802420. Epub 2018 Jun 25. PMID: 29847691.
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Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of ( E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters.

The Journal of organic chemistry

Xiong Q, Lin L, Zhao X, Lang J, Liu X, Feng X.
PMID: 30222927
J Org Chem. 2018 Oct 19;83(20):12527-12534. doi: 10.1021/acs.joc.8b01771. Epub 2018 Oct 03.

A highly regio-, diastereo-, and enantioselective Diels-Alder reaction of β,γ-unsaturated α-ketoesters with ( E)-1-phenyl dienes has been accomplished by using a stable and easily available chiral N,N'-dioxide/zinc(II) complex as catalyst. Only one isomer of the corresponding cyclohexenes with three...

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Xiong Q, Lin L, Zhao X, et al. Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of ( E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters. J Org Chem. 2018;83(20):12527-12534doi: 10.1021/acs.joc.8b01771.
Xiong, Q., Lin, L., Zhao, X., Lang, J., Liu, X., & Feng, X. (2018). Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of ( E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters. The Journal of organic chemistry, 83(20), 12527-12534. https://doi.org/10.1021/acs.joc.8b01771
Xiong, Qian, et al. "Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of ( E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters." The Journal of organic chemistry vol. 83,20 (2018): 12527-12534. doi: https://doi.org/10.1021/acs.joc.8b01771
Xiong Q, Lin L, Zhao X, Lang J, Liu X, Feng X. Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of ( E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters. J Org Chem. 2018 Oct 19;83(20):12527-12534. doi: 10.1021/acs.joc.8b01771. Epub 2018 Oct 03. PMID: 30222927.
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New entry to the enantioselective formation of substituted cyclohexenes bearing an all-carbon quaternary stereogenic center.

Chirality

Komine K, Urayama Y, Hosaka T, Fukuda H, Hatakeyama S, Ishihara J.
PMID: 31957912
Chirality. 2020 Mar;32(3):273-281. doi: 10.1002/chir.23173. Epub 2020 Jan 20.

Enantioselective formation of cyclohexene derivatives bearing an all-carbon quaternary stereogenic center is described. The racemic cyclohexenes are readily transformed to chiral substituted cyclohexenes in good yield with excellent enantioselectivity and diastereoselectivity by a palladium-mediated deracemization. The resulting products are...

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Komine K, Urayama Y, Hosaka T, et al. New entry to the enantioselective formation of substituted cyclohexenes bearing an all-carbon quaternary stereogenic center. Chirality. 2020;32(3):273-281doi: 10.1002/chir.23173.
Komine, K., Urayama, Y., Hosaka, T., Fukuda, H., Hatakeyama, S., & Ishihara, J. (2020). New entry to the enantioselective formation of substituted cyclohexenes bearing an all-carbon quaternary stereogenic center. Chirality, 32(3), 273-281. https://doi.org/10.1002/chir.23173
Komine, Keita, et al. "New entry to the enantioselective formation of substituted cyclohexenes bearing an all-carbon quaternary stereogenic center." Chirality vol. 32,3 (2020): 273-281. doi: https://doi.org/10.1002/chir.23173
Komine K, Urayama Y, Hosaka T, Fukuda H, Hatakeyama S, Ishihara J. New entry to the enantioselective formation of substituted cyclohexenes bearing an all-carbon quaternary stereogenic center. Chirality. 2020 Mar;32(3):273-281. doi: 10.1002/chir.23173. Epub 2020 Jan 20. PMID: 31957912.
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Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes.

Angewandte Chemie (International ed. in English)

Cho S, McLaren EJ, Wang Q.
PMID: 34644004
Angew Chem Int Ed Engl. 2021 Dec 06;60(50):26332-26336. doi: 10.1002/anie.202109482. Epub 2021 Nov 08.

Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates....

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Cho S, McLaren EJ, Wang Q. Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes. Angew Chem Int Ed Engl. 2021;60(50):26332-26336doi: 10.1002/anie.202109482.
Cho, S., McLaren, E. J., & Wang, Q. (2021). Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes. Angewandte Chemie (International ed. in English), 60(50), 26332-26336. https://doi.org/10.1002/anie.202109482
Cho, Seoyoung, et al. "Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes." Angewandte Chemie (International ed. in English) vol. 60,50 (2021): 26332-26336. doi: https://doi.org/10.1002/anie.202109482
Cho S, McLaren EJ, Wang Q. Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes. Angew Chem Int Ed Engl. 2021 Dec 06;60(50):26332-26336. doi: 10.1002/anie.202109482. Epub 2021 Nov 08. PMID: 34644004.
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Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure-activity relationship of its derivatives.

Bioorganic chemistry

Sun Z, Yang S, Xu C, Yi F, Cao L, Tian Y, Lin J, Xu X.
PMID: 34537516
Bioorg Chem. 2021 Nov;116:105333. doi: 10.1016/j.bioorg.2021.105333. Epub 2021 Sep 04.

Natural products--polyoxygenated cyclohexenes exhibited potent anti-tumor activity, such as zeylenone, which is a natural product isolated from Uvaria grandiflora Roxb. This article will attempt to establish a gram-scale synthesis method of (+)-zeylenone and explain the structure-activity relationship of this...

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Sun Z, Yang S, Xu C, et al. Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure-activity relationship of its derivatives. Bioorg Chem. 2021;116:105333doi: 10.1016/j.bioorg.2021.105333.
Sun, Z., Yang, S., Xu, C., Yi, F., Cao, L., Tian, Y., Lin, J., & Xu, X. (2021). Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure-activity relationship of its derivatives. Bioorganic chemistry, 116105333. https://doi.org/10.1016/j.bioorg.2021.105333
Sun, Zhonghao, et al. "Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure-activity relationship of its derivatives." Bioorganic chemistry vol. 116 (2021): 105333. doi: https://doi.org/10.1016/j.bioorg.2021.105333
Sun Z, Yang S, Xu C, Yi F, Cao L, Tian Y, Lin J, Xu X. Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure-activity relationship of its derivatives. Bioorg Chem. 2021 Nov;116:105333. doi: 10.1016/j.bioorg.2021.105333. Epub 2021 Sep 04. PMID: 34537516.
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