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Preparation and reductive transformations of vinylogous sulfonamides (beta-sulfonyl enamines), and application to the synthesis of indolizidines.

Organic & biomolecular chemistry

Michael JP, de Koning CB, Malefetse TJ, Yillah I.
PMID: 15565245
Org Biomol Chem. 2004 Dec 07;2(23):3510-7. doi: 10.1039/b413379j. Epub 2004 Nov 04.

Condensation between the methiodide salts of 1-alkylpyrrolidine-2-thiones and ethyl [(4-methylphenyl)sulfonyl]acetate or 1-[(4-methylphenyl)sulfonyl]propan-2-one afforded several 2-[[(4-methylphenyl)sulfonyl]methylene]pyrrolidines in good yield. These beta-sulfonyl enamines are sufficiently nucleophilic for cyclisation with internal electrophiles to give sulfone-substituted indolizines, potentially useful scaffolds for alkaloid synthesis....

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Michael JP, de Koning CB, Malefetse TJ, et al. Preparation and reductive transformations of vinylogous sulfonamides (beta-sulfonyl enamines), and application to the synthesis of indolizidines. Org Biomol Chem. 2004;2(23):3510-7doi: 10.1039/b413379j.
Michael, J. P., de Koning, C. B., Malefetse, T. J., & Yillah, I. (2004). Preparation and reductive transformations of vinylogous sulfonamides (beta-sulfonyl enamines), and application to the synthesis of indolizidines. Organic & biomolecular chemistry, 2(23), 3510-7. https://doi.org/10.1039/b413379j
Michael, Joseph P, et al. "Preparation and reductive transformations of vinylogous sulfonamides (beta-sulfonyl enamines), and application to the synthesis of indolizidines." Organic & biomolecular chemistry vol. 2,23 (2004): 3510-7. doi: https://doi.org/10.1039/b413379j
Michael JP, de Koning CB, Malefetse TJ, Yillah I. Preparation and reductive transformations of vinylogous sulfonamides (beta-sulfonyl enamines), and application to the synthesis of indolizidines. Org Biomol Chem. 2004 Dec 07;2(23):3510-7. doi: 10.1039/b413379j. Epub 2004 Nov 04. PMID: 15565245.
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Silylstannylation of highly functionalized acetylenes. synthesis of precursors for annulations via radical or Heck reactions.

Organic letters

Apte S, Radetich B, Shin S, RajanBabu TV.
PMID: 15496097
Org Lett. 2004 Oct 28;6(22):4053-6. doi: 10.1021/ol048265w.

[reaction: see text] Pd-catalyzed silylstannylation of acetylenes tolerates a variety of reactive functional groups (aldehydes, nonterminal acetylenes, epoxides, activated and unactivated olefins), providing easy access to precursors that can be converted into carbocyclic and heterocyclic compounds via free radical...

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Apte S, Radetich B, Shin S, et al. Silylstannylation of highly functionalized acetylenes. synthesis of precursors for annulations via radical or Heck reactions. Org Lett. 2004;6(22):4053-6doi: 10.1021/ol048265w.
Apte, S., Radetich, B., Shin, S., & RajanBabu, T. V. (2004). Silylstannylation of highly functionalized acetylenes. synthesis of precursors for annulations via radical or Heck reactions. Organic letters, 6(22), 4053-6. https://doi.org/10.1021/ol048265w
Apte, Sandeep, et al. "Silylstannylation of highly functionalized acetylenes. synthesis of precursors for annulations via radical or Heck reactions." Organic letters vol. 6,22 (2004): 4053-6. doi: https://doi.org/10.1021/ol048265w
Apte S, Radetich B, Shin S, RajanBabu TV. Silylstannylation of highly functionalized acetylenes. synthesis of precursors for annulations via radical or Heck reactions. Org Lett. 2004 Oct 28;6(22):4053-6. doi: 10.1021/ol048265w. PMID: 15496097.
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Theoretical analysis of Lewis basicity based on local electron-donating ability. Origin of basic strength of cyclic amines.

The Journal of organic chemistry

Ohwada T, Hirao H, Ogawa A.
PMID: 15497973
J Org Chem. 2004 Oct 29;69(22):7486-94. doi: 10.1021/jo0486589.

It has been experimentally established that the proton affinities (PA), as well as the solution basicities (pK(BH)(+)), of aziridine derivatives are much smaller than those of the corresponding pyrrolidines and piperidines, though the basic strength of azetidines is close...

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Ohwada T, Hirao H, Ogawa A. Theoretical analysis of Lewis basicity based on local electron-donating ability. Origin of basic strength of cyclic amines. J Org Chem. 2004;69(22):7486-94doi: 10.1021/jo0486589.
Ohwada, T., Hirao, H., & Ogawa, A. (2004). Theoretical analysis of Lewis basicity based on local electron-donating ability. Origin of basic strength of cyclic amines. The Journal of organic chemistry, 69(22), 7486-94. https://doi.org/10.1021/jo0486589
Ohwada, Tomohiko, et al. "Theoretical analysis of Lewis basicity based on local electron-donating ability. Origin of basic strength of cyclic amines." The Journal of organic chemistry vol. 69,22 (2004): 7486-94. doi: https://doi.org/10.1021/jo0486589
Ohwada T, Hirao H, Ogawa A. Theoretical analysis of Lewis basicity based on local electron-donating ability. Origin of basic strength of cyclic amines. J Org Chem. 2004 Oct 29;69(22):7486-94. doi: 10.1021/jo0486589. PMID: 15497973.
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An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions.

Organic & biomolecular chemistry

Liu XW, Le TN, Lu Y, Xiao Y, Ma J, Li X.
PMID: 18931808
Org Biomol Chem. 2008 Nov 07;6(21):3997-4003. doi: 10.1039/b811581h. Epub 2008 Sep 04.

Chiral pyrrolidine-based phosphinyl oxides were synthesized and their performance as organocatalysts for asymmetric direct aldol reactions was evaluated. High enantioselectivities and diastereoselectivies were achieved for a range of cyclic ketones and aromatic aldehydes.

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Liu XW, Le TN, Lu Y, et al. An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions. Org Biomol Chem. 2008;6(21):3997-4003doi: 10.1039/b811581h.
Liu, X. W., Le, T. N., Lu, Y., Xiao, Y., Ma, J., & Li, X. (2008). An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions. Organic & biomolecular chemistry, 6(21), 3997-4003. https://doi.org/10.1039/b811581h
Liu, Xue-Wei, et al. "An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions." Organic & biomolecular chemistry vol. 6,21 (2008): 3997-4003. doi: https://doi.org/10.1039/b811581h
Liu XW, Le TN, Lu Y, Xiao Y, Ma J, Li X. An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions. Org Biomol Chem. 2008 Nov 07;6(21):3997-4003. doi: 10.1039/b811581h. Epub 2008 Sep 04. PMID: 18931808.
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Aminals as substrates for sulfur ylides: a synthesis of functionalized aziridines and N-heterocycles.

Organic letters

Kokotos CG, Aggarwal VK.
PMID: 17465558
Org Lett. 2007 May 24;9(11):2099-102. doi: 10.1021/ol070507f. Epub 2007 Apr 28.

Sulfur ylides stabilized by Ar, vinyl, or amide groups react with five-membered-ring tert-butylsulfinyl aminals to give functionalized chiral, nonracemic aziridines in high yield and with good selectivities (up to 15:1 trans:cis, up to >95:5 trans dr, always >95:5 cis...

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Kokotos CG, Aggarwal VK. Aminals as substrates for sulfur ylides: a synthesis of functionalized aziridines and N-heterocycles. Org Lett. 2007;9(11):2099-102doi: 10.1021/ol070507f.
Kokotos, C. G., & Aggarwal, V. K. (2007). Aminals as substrates for sulfur ylides: a synthesis of functionalized aziridines and N-heterocycles. Organic letters, 9(11), 2099-102. https://doi.org/10.1021/ol070507f
Kokotos, Christoforos G, and Aggarwal, Varinder K. "Aminals as substrates for sulfur ylides: a synthesis of functionalized aziridines and N-heterocycles." Organic letters vol. 9,11 (2007): 2099-102. doi: https://doi.org/10.1021/ol070507f
Kokotos CG, Aggarwal VK. Aminals as substrates for sulfur ylides: a synthesis of functionalized aziridines and N-heterocycles. Org Lett. 2007 May 24;9(11):2099-102. doi: 10.1021/ol070507f. Epub 2007 Apr 28. PMID: 17465558.
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Stereochemical memory effects in alkene radical cation/anion contact ion pairs: effect of substituents, and models for diastereoselectivity.

Journal of the American Chemical Society

Crich D, Ranganathan K.
PMID: 15998099
J Am Chem Soc. 2005 Jul 13;127(27):9924-9. doi: 10.1021/ja051657t.

A series of 12 stereochemically defined 2,m-dimethyl- and 2,m,n-trimethyl-6-benzylamino-2-nitro-3-(diphenylphosphatoxy)hexanes have been synthesized and their cyclization reactions leading to di- and trisubstituted N-benzyl pyrrolidines examined in the presence of tributyltin hydride and azoisobutyronitrile in benzene at reflux. The cyclizations are...

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Crich D, Ranganathan K. Stereochemical memory effects in alkene radical cation/anion contact ion pairs: effect of substituents, and models for diastereoselectivity. J Am Chem Soc. 2005;127(27):9924-9doi: 10.1021/ja051657t.
Crich, D., & Ranganathan, K. (2005). Stereochemical memory effects in alkene radical cation/anion contact ion pairs: effect of substituents, and models for diastereoselectivity. Journal of the American Chemical Society, 127(27), 9924-9. https://doi.org/10.1021/ja051657t
Crich, David, and Ranganathan, Krishnakumar. "Stereochemical memory effects in alkene radical cation/anion contact ion pairs: effect of substituents, and models for diastereoselectivity." Journal of the American Chemical Society vol. 127,27 (2005): 9924-9. doi: https://doi.org/10.1021/ja051657t
Crich D, Ranganathan K. Stereochemical memory effects in alkene radical cation/anion contact ion pairs: effect of substituents, and models for diastereoselectivity. J Am Chem Soc. 2005 Jul 13;127(27):9924-9. doi: 10.1021/ja051657t. PMID: 15998099.
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Microwave-assisted [3 + 2] cycloadditions of azomethine ylides.

Organic letters

Bashiardes G, Safir I, Mohamed AS, Barbot F, Laduranty J.
PMID: 14653706
Org Lett. 2003 Dec 11;5(25):4915-8. doi: 10.1021/ol0361195.

The microwave-assisted intramolecular [3 + 2] cycloaddition reaction of azomethine ylides to activated and nonactivated alkenes and alkynes is described. The procedure allows the synthesis of pyrrolidines and pyrrole products in good to excellent overall yields in short reaction...

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Bashiardes G, Safir I, Mohamed AS, et al. Microwave-assisted [3 + 2] cycloadditions of azomethine ylides. Org Lett. 2003;5(25):4915-8doi: 10.1021/ol0361195.
Bashiardes, G., Safir, I., Mohamed, A. S., Barbot, F., & Laduranty, J. (2003). Microwave-assisted [3 + 2] cycloadditions of azomethine ylides. Organic letters, 5(25), 4915-8. https://doi.org/10.1021/ol0361195
Bashiardes, George, et al. "Microwave-assisted [3 + 2] cycloadditions of azomethine ylides." Organic letters vol. 5,25 (2003): 4915-8. doi: https://doi.org/10.1021/ol0361195
Bashiardes G, Safir I, Mohamed AS, Barbot F, Laduranty J. Microwave-assisted [3 + 2] cycloadditions of azomethine ylides. Org Lett. 2003 Dec 11;5(25):4915-8. doi: 10.1021/ol0361195. PMID: 14653706.
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Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds.

Beilstein journal of organic chemistry

Maison W, Büchert M, Deppermann N.
PMID: 18088413
Beilstein J Org Chem. 2007 Dec 18;3:48. doi: 10.1186/1860-5397-3-48.

BACKGROUND: Tandem olefin metathesis sequences are known to be versatile for the generation of natural product scaffolds and have also been used for ring opening of strained carbo- and heterocycles. In this paper we demonstrate the potential of these...

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Maison W, Büchert M, Deppermann N. Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds. Beilstein J Org Chem. 2007;3:48doi: 10.1186/1860-5397-3-48.
Maison, W., Büchert, M., & Deppermann, N. (2007). Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds. Beilstein journal of organic chemistry, 348. https://doi.org/10.1186/1860-5397-3-48
Maison, Wolfgang, et al. "Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds." Beilstein journal of organic chemistry vol. 3 (2007): 48. doi: https://doi.org/10.1186/1860-5397-3-48
Maison W, Büchert M, Deppermann N. Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds. Beilstein J Org Chem. 2007 Dec 18;3:48. doi: 10.1186/1860-5397-3-48. PMID: 18088413; PMCID: PMC2200670.
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Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines.

European journal of organic chemistry

Wolfe JP.
PMID: 20577649
European J Org Chem. 2007 Feb;2007(4):571-582.

Substituted tetrahydrofuran and pyrrolidine moieties are displayed in a wide range of interesting biologically active molecules. The Pd-catalyzed carboetherification or carboamination of γ-hydroxy- and γ-aminoalkenes is a powerful tool for the construction of these heterocycles, as it is convergent...

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Wolfe JP. Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines. European J Org Chem. 2007;2007(4):571-582
Wolfe, J. P. (2007). Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines. European journal of organic chemistry, 2007(4), 571-582.
Wolfe, John P. "Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines." European journal of organic chemistry vol. 2007,4 (2007): 571-582.
Wolfe JP. Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines. European J Org Chem. 2007 Feb;2007(4):571-582. PMID: 20577649; PMCID: PMC2890284.
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Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination.

Organometallics

Watson DA, Chiu M, Bergman RG.
PMID: 19079735
Organometallics. 2006 Sep 25;25(20):4731-4733. doi: 10.1021/om0606791.

In situ combination of diphosphinic amides and Zr(NMe(2))(4) results in the formation of chiral zirconium bis(amido) complexes. The complexes are competent catalysts for intramolecular asymmetric alkene hydroamintion, providing piperidines and pyrrolidines in up to 80% ee and high yield....

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Watson DA, Chiu M, Bergman RG. Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination. Organometallics. 2006;25(20):4731-4733doi: 10.1021/om0606791.
Watson, D. A., Chiu, M., & Bergman, R. G. (2006). Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination. Organometallics, 25(20), 4731-4733. https://doi.org/10.1021/om0606791
Watson, Donald A, et al. "Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination." Organometallics vol. 25,20 (2006): 4731-4733. doi: https://doi.org/10.1021/om0606791
Watson DA, Chiu M, Bergman RG. Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination. Organometallics. 2006 Sep 25;25(20):4731-4733. doi: 10.1021/om0606791. PMID: 19079735; PMCID: PMC2600731.
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Organocatalytic enantioselective synthesis of highly functionalized polysubstituted pyrrolidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ruiz N, Reyes E, Vicario JL, Badía D, Carrillo L, Uria U.
PMID: 18767107
Chemistry. 2008;14(30):9357-67. doi: 10.1002/chem.200800788.

The organocatalytic conjugate addition of different aldehydes to beta-nitroacrolein dimethyl acetal, generating the corresponding highly functionalized nitroaldehydes in high yields and with high stereoselectivities, has been studied in detail. These transformations have been achieved by using both readily available...

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Ruiz N, Reyes E, Vicario JL, et al. Organocatalytic enantioselective synthesis of highly functionalized polysubstituted pyrrolidines. Chemistry. 2008;14(30):9357-67doi: 10.1002/chem.200800788.
Ruiz, N., Reyes, E., Vicario, J. L., Badía, D., Carrillo, L., & Uria, U. (2008). Organocatalytic enantioselective synthesis of highly functionalized polysubstituted pyrrolidines. Chemistry (Weinheim an der Bergstrasse, Germany), 14(30), 9357-67. https://doi.org/10.1002/chem.200800788
Ruiz, Nerea, et al. "Organocatalytic enantioselective synthesis of highly functionalized polysubstituted pyrrolidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 14,30 (2008): 9357-67. doi: https://doi.org/10.1002/chem.200800788
Ruiz N, Reyes E, Vicario JL, Badía D, Carrillo L, Uria U. Organocatalytic enantioselective synthesis of highly functionalized polysubstituted pyrrolidines. Chemistry. 2008;14(30):9357-67. doi: 10.1002/chem.200800788. PMID: 18767107.
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Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Synlett : accounts and rapid communications in synthetic organic chemistry

Wolfe JP.
PMID: 19183704
Synlett. 2006 Nov 13;2007(4):571-582. doi: 10.1002/ejoc.200600767.

The development of Pd-catalyzed carboetherification and carboamination reactions between aryl/alkenyl halides and alkenes bearing pendant heteroatoms is described. These transformations effect the stereoselective construction of useful heterocycles such as tetrahydrofurans, pyrrolidines, imidazolidin-2-ones, isoxazolidines, and piperazines. The scope, limitations, and...

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Wolfe JP. Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions. Synlett. 2006;2007(4):571-582doi: 10.1002/ejoc.200600767.
Wolfe, J. P. (2006). Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions. Synlett : accounts and rapid communications in synthetic organic chemistry, 2007(4), 571-582. https://doi.org/10.1002/ejoc.200600767
Wolfe, John P. "Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions." Synlett : accounts and rapid communications in synthetic organic chemistry vol. 2007,4 (2006): 571-582. doi: https://doi.org/10.1002/ejoc.200600767
Wolfe JP. Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions. Synlett. 2006 Nov 13;2007(4):571-582. doi: 10.1002/ejoc.200600767. PMID: 19183704; PMCID: PMC2633094.
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Showing 25 to 36 of 366 entries