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Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones

Louis Stokes Alliances for Minority Participation AND Program Evaluation

Murelli RP.
GSID: AQhSaAM0Er0J
A Munoz, RP Murelli - Tetrahedron letters, 2012 - Elsevier

In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), γ-methyl-γ-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in...

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Munoz, A., & Murelli, R. P. (2012). Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones. Tetrahedron letters, 53(50), 6779-6781.
Munoz, Alberto, and Ryan P. Murelli. "Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones." Tetrahedron letters 53.50 (2012): 6779-6781.
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Chemistry of N-methoxy-N-methylamides. Applications in synthesis. A review

EPSCoR Research Infrastructure Improvement Program AND Program Evaluation

Sibi MP.
GSID: zZI248zYKJAJ
MP Sibi - Organic preparations and procedures international, 1993 - Taylor & Francis

Since the initial report of Nahm and Weinreb'on the use of N-methoxy-N-methylamides 1 as carbonyl equivalents, this functional group has enjoyed tremendous popularity (Scheme 1). The main reasons for the utility of this synthon are the ease of preparation,...

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Sibi, M. P. (1993). Chemistry of N-methoxy-N-methylamides. Applications in synthesis. A review. Organic preparations and procedures international, 25(1), 15-40.
Sibi, Mukund P. "Chemistry of N-methoxy-N-methylamides. Applications in synthesis. A review." Organic preparations and procedures international 25.1 (1993): 15-40.
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Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols.

Chemistry (Weinheim an der Bergstrasse, Germany)

Bodzioch A, Marciniak B, Różycka-Sokołowska E, Jeszka JK, Uznański P, Kania S, Kuliński J, Bałczewski P.
PMID: 22438194
Chemistry. 2012 Apr 16;18(16):4866-76. doi: 10.1002/chem.201101909. Epub 2012 Mar 21.

A new modification of the Friedel-Crafts type intramolecular cyclization involving O-protected ortho-acetal diarylmethanols as a new type of reactant, was carried out for the first time in a medium containing a large amount of water at room temperature and...

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Bodzioch A, Marciniak B, Różycka-Sokołowska E, et al. Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry. 2012;18(16):4866-76doi: 10.1002/chem.201101909.
Bodzioch, A., Marciniak, B., Różycka-Sokołowska, E., Jeszka, J. K., Uznański, P., Kania, S., Kuliński, J., & Bałczewski, P. (2012). Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry (Weinheim an der Bergstrasse, Germany), 18(16), 4866-76. https://doi.org/10.1002/chem.201101909
Bodzioch, Agnieszka, et al. "Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 18,16 (2012): 4866-76. doi: https://doi.org/10.1002/chem.201101909
Bodzioch A, Marciniak B, Różycka-Sokołowska E, Jeszka JK, Uznański P, Kania S, Kuliński J, Bałczewski P. Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry. 2012 Apr 16;18(16):4866-76. doi: 10.1002/chem.201101909. Epub 2012 Mar 21. PMID: 22438194.
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Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives.

Organic & biomolecular chemistry

Weber AK, Schachtner J, Fichtler R, Leermann TM, Neudörfl JM, Jacobi von Wangelin A.
PMID: 24924419
Org Biomol Chem. 2014 Jul 28;12(28):5267-77. doi: 10.1039/c4ob00913d.

Structurally diverse carbocycles with two vicinal nitrogen-substituents were prepared in expedient three-component reactions from simple amines, aldehydes, and nitroalkenes. trans,trans-6-Nitrocyclohex-2-enyl amines were obtained in a one-pot domino reaction involving condensation, tautomerisation, conjugate addition, and nitro-Mannich cyclisation. Upon employment of...

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Weber AK, Schachtner J, Fichtler R, et al. Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives. Org Biomol Chem. 2014;12(28):5267-77doi: 10.1039/c4ob00913d.
Weber, A. K., Schachtner, J., Fichtler, R., Leermann, T. M., Neudörfl, J. M., & Jacobi von Wangelin, A. (2014). Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives. Organic & biomolecular chemistry, 12(28), 5267-77. https://doi.org/10.1039/c4ob00913d
Weber, Anna K, et al. "Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives." Organic & biomolecular chemistry vol. 12,28 (2014): 5267-77. doi: https://doi.org/10.1039/c4ob00913d
Weber AK, Schachtner J, Fichtler R, Leermann TM, Neudörfl JM, Jacobi von Wangelin A. Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives. Org Biomol Chem. 2014 Jul 28;12(28):5267-77. doi: 10.1039/c4ob00913d. PMID: 24924419.
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Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals.

Communicative & integrative biology

de Lacy Costello BP, Adamatzky AI.
PMID: 24265848
Commun Integr Biol. 2013 Sep 01;6(5):e25030. doi: 10.4161/cib.25030. Epub 2013 Jun 14.

The chemotaxis behavior of the plasmodial stage of the true slime mold Physarum Polycephalum was assessed when given a binary choice between two volatile organic chemicals (VOCs) placed in its environment. All possible binary combinations were tested between 19...

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de Lacy Costello BP, Adamatzky AI. Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals. Commun Integr Biol. 2013;6(5):e25030doi: 10.4161/cib.25030.
de Lacy Costello, B. P., & Adamatzky, A. I. (2013). Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals. Communicative & integrative biology, 6(5), e25030. https://doi.org/10.4161/cib.25030
de Lacy Costello, Ben P J, and Adamatzky, Andrew I. "Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals." Communicative & integrative biology vol. 6,5 (2013): e25030. doi: https://doi.org/10.4161/cib.25030
de Lacy Costello BP, Adamatzky AI. Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals. Commun Integr Biol. 2013 Sep 01;6(5):e25030. doi: 10.4161/cib.25030. Epub 2013 Jun 14. PMID: 24265848; PMCID: PMC3829954.
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Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis.

Journal of chemical ecology

Burger BV, Tien FC, Le Roux M, Mo WP.
PMID: 24227582
J Chem Ecol. 1996 Apr;22(4):739-64. doi: 10.1007/BF02033583.

Using electron impact and chemical ionization mass spectrometry with methane and nitric oxide as reactant gases in conjunction with mass spectral analysis of the dimethyl disulfide derivatives of unsaturated constituents, 51 compounds have been identified in addition to the...

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Burger BV, Tien FC, Le Roux M, et al. Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis. J Chem Ecol. 1996;22(4):739-64doi: 10.1007/BF02033583.
Burger, B. V., Tien, F. C., Le Roux, M., & Mo, W. P. (1996). Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis. Journal of chemical ecology, 22(4), 739-64. https://doi.org/10.1007/BF02033583
Burger, B V, et al. "Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis." Journal of chemical ecology vol. 22,4 (1996): 739-64. doi: https://doi.org/10.1007/BF02033583
Burger BV, Tien FC, Le Roux M, Mo WP. Mammalian exocrine secretions: X. constituents of preorbital secretion of grysbok,Raphicerus melanotis. J Chem Ecol. 1996 Apr;22(4):739-64. doi: 10.1007/BF02033583. PMID: 24227582.
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The hierarchical construction of cross-junctions of molecular wires with covalent and noncovalent interactions at the liquid/solid interface.

Chemical communications (Cambridge, England)

Yu Y, Yang L, Liu C, Tian WQ, Wang Y, Lei S.
PMID: 27296368
Chem Commun (Camb). 2016 Jul 07;52(53):8317-20. doi: 10.1039/c6cc02975b. Epub 2016 Jun 14.

Hierarchical networks, constructed by non-covalent bond stabilized cross-junctions of covalent one-dimensional molecular wires, are synergistically formed at the liquid/solid interface through in situ on-surface condensation of aromatic amines and aldehydes. Our investigation demonstrates the significant impact of the concentration...

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Yu Y, Yang L, Liu C, et al. The hierarchical construction of cross-junctions of molecular wires with covalent and noncovalent interactions at the liquid/solid interface. Chem Commun (Camb). 2016;52(53):8317-20doi: 10.1039/c6cc02975b.
Yu, Y., Yang, L., Liu, C., Tian, W. Q., Wang, Y., & Lei, S. (2016). The hierarchical construction of cross-junctions of molecular wires with covalent and noncovalent interactions at the liquid/solid interface. Chemical communications (Cambridge, England), 52(53), 8317-20. https://doi.org/10.1039/c6cc02975b
Yu, Yanxia, et al. "The hierarchical construction of cross-junctions of molecular wires with covalent and noncovalent interactions at the liquid/solid interface." Chemical communications (Cambridge, England) vol. 52,53 (2016): 8317-20. doi: https://doi.org/10.1039/c6cc02975b
Yu Y, Yang L, Liu C, Tian WQ, Wang Y, Lei S. The hierarchical construction of cross-junctions of molecular wires with covalent and noncovalent interactions at the liquid/solid interface. Chem Commun (Camb). 2016 Jul 07;52(53):8317-20. doi: 10.1039/c6cc02975b. Epub 2016 Jun 14. PMID: 27296368.
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Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane.

Organic letters

Kawamoto T, Okada T, Curran DP, Ryu I.
PMID: 23590524
Org Lett. 2013 May 03;15(9):2144-7. doi: 10.1021/ol4006294. Epub 2013 Apr 16.

A hydroxymethylation reaction of a variety of iodoarenes proceeded effectively in the presence of CO, NHC-borane, diMeImd-BH3 (2) as a radical mediator, and a catalytic amount of AIBN. The reaction took place chemoselectively at the aryl-iodine bond but not...

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Kawamoto T, Okada T, Curran DP, et al. Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Org Lett. 2013;15(9):2144-7doi: 10.1021/ol4006294.
Kawamoto, T., Okada, T., Curran, D. P., & Ryu, I. (2013). Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Organic letters, 15(9), 2144-7. https://doi.org/10.1021/ol4006294
Kawamoto, Takuji, et al. "Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane." Organic letters vol. 15,9 (2013): 2144-7. doi: https://doi.org/10.1021/ol4006294
Kawamoto T, Okada T, Curran DP, Ryu I. Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Org Lett. 2013 May 03;15(9):2144-7. doi: 10.1021/ol4006294. Epub 2013 Apr 16. PMID: 23590524.
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Regio- and Chemoselective Kumada-Tamao-Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions.

Journal of the American Chemical Society

Cong X, Tang H, Zeng X.
PMID: 26469380
J Am Chem Soc. 2015 Nov 18;137(45):14367-72. doi: 10.1021/jacs.5b08621. Epub 2015 Nov 04.

Acting as an environmentally benign synthetic tool, the cross-coupling reactions with aryl ethers via C-O bond activation have attracted broad interest. However, the functionalizations of C-O bonds are mainly limited to nickel catalysis, and selectivity has long been a...

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Cong X, Tang H, Zeng X. Regio- and Chemoselective Kumada-Tamao-Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions. J Am Chem Soc. 2015;137(45):14367-72doi: 10.1021/jacs.5b08621.
Cong, X., Tang, H., & Zeng, X. (2015). Regio- and Chemoselective Kumada-Tamao-Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions. Journal of the American Chemical Society, 137(45), 14367-72. https://doi.org/10.1021/jacs.5b08621
Cong, Xuefeng, et al. "Regio- and Chemoselective Kumada-Tamao-Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions." Journal of the American Chemical Society vol. 137,45 (2015): 14367-72. doi: https://doi.org/10.1021/jacs.5b08621
Cong X, Tang H, Zeng X. Regio- and Chemoselective Kumada-Tamao-Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions. J Am Chem Soc. 2015 Nov 18;137(45):14367-72. doi: 10.1021/jacs.5b08621. Epub 2015 Nov 04. PMID: 26469380.
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Chemical compositions of the volatile extracts from seeds of Dendranthema nankingense and Borago officinalis.

Journal of food and drug analysis

Wu S, Xu T, Huang D.
PMID: 28911380
J Food Drug Anal. 2015 Jun;23(2):253-259. doi: 10.1016/j.jfda.2014.10.006. Epub 2014 Dec 03.

Volatile extracts from the seeds of Dendranthema nankingense Hand.-Mazz. and Borago officinalis L. were prepared using simultaneous distillation and extraction, and analyzed with gas chromatography-mass spectrometry on two capillary gas chromatography columns of different polarity. Ninety-five volatile compounds were...

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Wu S, Xu T, Huang D. Chemical compositions of the volatile extracts from seeds of Dendranthema nankingense and Borago officinalis. J Food Drug Anal. 2014;23(2):253-259doi: 10.1016/j.jfda.2014.10.006.
Wu, S., Xu, T., & Huang, D. (2015). Chemical compositions of the volatile extracts from seeds of Dendranthema nankingense and Borago officinalis. Journal of food and drug analysis, 23(2), 253-259. https://doi.org/10.1016/j.jfda.2014.10.006
Wu, Shimin, et al. "Chemical compositions of the volatile extracts from seeds of Dendranthema nankingense and Borago officinalis." Journal of food and drug analysis vol. 23,2 (2015): 253-259. doi: https://doi.org/10.1016/j.jfda.2014.10.006
Wu S, Xu T, Huang D. Chemical compositions of the volatile extracts from seeds of Dendranthema nankingense and Borago officinalis. J Food Drug Anal. 2015 Jun;23(2):253-259. doi: 10.1016/j.jfda.2014.10.006. Epub 2014 Dec 03. PMID: 28911380.
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Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes.

The Journal of organic chemistry

Yue Y, Peng J, Wang D, Bian Y, Sun P, Chen C.
PMID: 28472886
J Org Chem. 2017 May 19;82(10):5481-5486. doi: 10.1021/acs.joc.7b00640. Epub 2017 May 11.

The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh

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Yue Y, Peng J, Wang D, et al. Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes. J Org Chem. 2017;82(10):5481-5486doi: 10.1021/acs.joc.7b00640.
Yue, Y., Peng, J., Wang, D., Bian, Y., Sun, P., & Chen, C. (2017). Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes. The Journal of organic chemistry, 82(10), 5481-5486. https://doi.org/10.1021/acs.joc.7b00640
Yue, Yixia, et al. "Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes." The Journal of organic chemistry vol. 82,10 (2017): 5481-5486. doi: https://doi.org/10.1021/acs.joc.7b00640
Yue Y, Peng J, Wang D, Bian Y, Sun P, Chen C. Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes. J Org Chem. 2017 May 19;82(10):5481-5486. doi: 10.1021/acs.joc.7b00640. Epub 2017 May 11. PMID: 28472886.
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Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization.

Chemical record (New York, N.Y.)

Chelucci G, Porcheddu A.
PMID: 27524555
Chem Rec. 2017 Feb;17(2):200-216. doi: 10.1002/tcr.201600083. Epub 2016 Aug 15.

Efficient ruthenium-, rhodium-, palladium-, copper- and iridium-catalysed methodologies have been recently developed for the synthesis of quinolines by the reaction of 2-aminobenzyl alcohols with carbonyl compounds (aldehydes and ketones) or the related alcohols. The reaction is assumed to proceed...

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Chelucci G, Porcheddu A. Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chem Rec. 2016;17(2):200-216doi: 10.1002/tcr.201600083.
Chelucci, G., & Porcheddu, A. (2017). Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chemical record (New York, N.Y.), 17(2), 200-216. https://doi.org/10.1002/tcr.201600083
Chelucci, Giorgio, and Porcheddu, Andrea. "Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization." Chemical record (New York, N.Y.) vol. 17,2 (2017): 200-216. doi: https://doi.org/10.1002/tcr.201600083
Chelucci G, Porcheddu A. Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chem Rec. 2017 Feb;17(2):200-216. doi: 10.1002/tcr.201600083. Epub 2016 Aug 15. PMID: 27524555.
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Showing 1 to 12 of 6915 entries