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Highly stereoselective intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanides.

Journal of the American Chemical Society

Hong S, Marks TJ.
PMID: 12095317
J Am Chem Soc. 2002 Jul 10;124(27):7886-7. doi: 10.1021/ja020226x.

Efficient intramolecular hydroamination/cyclization of primary and secondary conjugated aminodienes can be effected by using organolanthanide precatalysts of the type Cp'2LnCH(TMS)2 (Cp' = eta5-Me5C5; Ln = La, Sm, Y; TMS = SiMe3) and CGCSmN(TMS)2 (CGC = Me2Si(eta5-Me4C5)(tBuN)). The transformation proceeds...

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Hong S, Marks TJ. Highly stereoselective intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanides. J Am Chem Soc. 2002;124(27):7886-7doi: 10.1021/ja020226x.
Hong, S., & Marks, T. J. (2002). Highly stereoselective intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanides. Journal of the American Chemical Society, 124(27), 7886-7. https://doi.org/10.1021/ja020226x
Hong, Sukwon, and Marks, Tobin J. "Highly stereoselective intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanides." Journal of the American Chemical Society vol. 124,27 (2002): 7886-7. doi: https://doi.org/10.1021/ja020226x
Hong S, Marks TJ. Highly stereoselective intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanides. J Am Chem Soc. 2002 Jul 10;124(27):7886-7. doi: 10.1021/ja020226x. PMID: 12095317.
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An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines.

The Journal of organic chemistry

Wu XD, Khim SK, Zhang X, Cederstrom EM, Mariano PS.
PMID: 11672082
J Org Chem. 1998 Feb 06;63(3):841-859. doi: 10.1021/jo971706n.

Studies focusing on the development and application of a new oxidative methodology for promoting Mannich cyclizations have been conducted. The general features of these processes were explored with selected alpha-silylamino and alpha-silylamido allyl- and vinylsilanes. Representative conditions for affecting...

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Wu XD, Khim SK, Zhang X, et al. An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines. J Org Chem. 1998;63(3):841-859doi: 10.1021/jo971706n.
Wu, X. D., Khim, S. K., Zhang, X., Cederstrom, E. M., & Mariano, P. S. (1998). An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines. The Journal of organic chemistry, 63(3), 841-859. https://doi.org/10.1021/jo971706n
Wu, Xiao-Dong, et al. "An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines." The Journal of organic chemistry vol. 63,3 (1998): 841-859. doi: https://doi.org/10.1021/jo971706n
Wu XD, Khim SK, Zhang X, Cederstrom EM, Mariano PS. An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines. J Org Chem. 1998 Feb 06;63(3):841-859. doi: 10.1021/jo971706n. PMID: 11672082.
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Organolanthanide-catalyzed intramolecular hydroamination/cyclization/bicyclization of sterically encumbered substrates. Scope, selectivity, and catalyst thermal stability for amine-tethered unactivated 1,2-disubstituted alkenes.

The Journal of organic chemistry

Ryu JS, Marks TJ, McDonald FE.
PMID: 14961651
J Org Chem. 2004 Feb 20;69(4):1038-52. doi: 10.1021/jo035417c.

This paper reports the organolanthanide-catalyzed intramolecular hydroamination/cyclization of amine-tethered unactivated 1,2-disubstituted alkenes to afford the corresponding mono- and disubstituted pyrrolidines and piperidines using coordinatively unsaturated complexes of the type (eta(5)-Me(5)C(5))(2)LnCH(TMS)(2) (Ln = La, Sm), [Me(2)Si(eta(5)-Me(4)C(5))(2)]SmCH(TMS)(2), and [Me(2)Si(eta(5)-Me(4)C(5))((t)BuN)]LnE(TMS)(2) (Ln =...

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Ryu JS, Marks TJ, McDonald FE. Organolanthanide-catalyzed intramolecular hydroamination/cyclization/bicyclization of sterically encumbered substrates. Scope, selectivity, and catalyst thermal stability for amine-tethered unactivated 1,2-disubstituted alkenes. J Org Chem. 2004;69(4):1038-52doi: 10.1021/jo035417c.
Ryu, J. S., Marks, T. J., & McDonald, F. E. (2004). Organolanthanide-catalyzed intramolecular hydroamination/cyclization/bicyclization of sterically encumbered substrates. Scope, selectivity, and catalyst thermal stability for amine-tethered unactivated 1,2-disubstituted alkenes. The Journal of organic chemistry, 69(4), 1038-52. https://doi.org/10.1021/jo035417c
Ryu, Jae-Sang, et al. "Organolanthanide-catalyzed intramolecular hydroamination/cyclization/bicyclization of sterically encumbered substrates. Scope, selectivity, and catalyst thermal stability for amine-tethered unactivated 1,2-disubstituted alkenes." The Journal of organic chemistry vol. 69,4 (2004): 1038-52. doi: https://doi.org/10.1021/jo035417c
Ryu JS, Marks TJ, McDonald FE. Organolanthanide-catalyzed intramolecular hydroamination/cyclization/bicyclization of sterically encumbered substrates. Scope, selectivity, and catalyst thermal stability for amine-tethered unactivated 1,2-disubstituted alkenes. J Org Chem. 2004 Feb 20;69(4):1038-52. doi: 10.1021/jo035417c. PMID: 14961651.
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A stereocontrolled access to ring-fused piperidines through a formal [2+2+2] process.

Organic letters

Godineau E, Schäfer C, Landais Y.
PMID: 17020324
Org Lett. 2006 Oct 12;8(21):4871-4. doi: 10.1021/ol061914e.

[reaction: see text] A formal [2+2+2] process has been devised that allows the stereocontrolled formation of ring-fused piperidines from allylsilanes possessing an oxime moiety. The cascade involves an intermolecular radical addition of an alpha-iodoacetate onto an allylsilane double bond,...

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Godineau E, Schäfer C, Landais Y. A stereocontrolled access to ring-fused piperidines through a formal [2+2+2] process. Org Lett. 2006;8(21):4871-4doi: 10.1021/ol061914e.
Godineau, E., Schäfer, C., & Landais, Y. (2006). A stereocontrolled access to ring-fused piperidines through a formal [2+2+2] process. Organic letters, 8(21), 4871-4. https://doi.org/10.1021/ol061914e
Godineau, Edouard, et al. "A stereocontrolled access to ring-fused piperidines through a formal [2+2+2] process." Organic letters vol. 8,21 (2006): 4871-4. doi: https://doi.org/10.1021/ol061914e
Godineau E, Schäfer C, Landais Y. A stereocontrolled access to ring-fused piperidines through a formal [2+2+2] process. Org Lett. 2006 Oct 12;8(21):4871-4. doi: 10.1021/ol061914e. PMID: 17020324.
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Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines.

Chemical communications (Cambridge, England)

Kokotos CG, Aggarwal VK.
PMID: 16703139
Chem Commun (Camb). 2006 May 28;(20):2156-8. doi: 10.1039/b602226j. Epub 2006 Apr 13.

Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enantioselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.

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Kokotos CG, Aggarwal VK. Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines. Chem Commun (Camb). 2006;(20):2156-8doi: 10.1039/b602226j.
Kokotos, C. G., & Aggarwal, V. K. (2006). Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines. Chemical communications (Cambridge, England), (20), 2156-8. https://doi.org/10.1039/b602226j
Kokotos, Christoforos G, and Aggarwal, Varinder K. "Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines." Chemical communications (Cambridge, England) vol. ,20 (2006): 2156-8. doi: https://doi.org/10.1039/b602226j
Kokotos CG, Aggarwal VK. Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines. Chem Commun (Camb). 2006 May 28;(20):2156-8. doi: 10.1039/b602226j. Epub 2006 Apr 13. PMID: 16703139.
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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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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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Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization.

Organic letters

Lam HW, Murray GJ, Firth JD.
PMID: 16321037
Org Lett. 2005 Dec 08;7(25):5743-6. doi: 10.1021/ol052599j.

[chemical reaction: see text]. 4-Hydroxypiperidin-2-ones may be prepared in highly diastereoselective fashion using a Cu(I)-catalyzed reductive aldol cyclization of alpha,beta-unsaturated amides with ketones. Used in combination with proline-catalyzed asymmetric Mannich reactions, this methodology enables the enantioselective synthesis of more...

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Lam HW, Murray GJ, Firth JD. Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization. Org Lett. 2005;7(25):5743-6doi: 10.1021/ol052599j.
Lam, H. W., Murray, G. J., & Firth, J. D. (2005). Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization. Organic letters, 7(25), 5743-6. https://doi.org/10.1021/ol052599j
Lam, Hon Wai, et al. "Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization." Organic letters vol. 7,25 (2005): 5743-6. doi: https://doi.org/10.1021/ol052599j
Lam HW, Murray GJ, Firth JD. Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization. Org Lett. 2005 Dec 08;7(25):5743-6. doi: 10.1021/ol052599j. PMID: 16321037.
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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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Platinum-catalyzed Michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of alpha,beta-sp3 C-H bonds.

The Journal of organic chemistry

Xia XF, Shu XZ, Ji KG, Yang YF, Ali S, Shaukat A, Liu XY, Liang YM.
PMID: 20345090
J Org Chem. 2010 May 07;75(9):2893-902. doi: 10.1021/jo100133z.

A mild platinum-catalyzed oxidative dehydrogenation of alpha,beta-C(sp(3))-H bonds of tertiary amines in the presence of ambient oxygen is revealed, and the in situ formed enamines subsequently reacting with various nitroolefins resulted in the development of two one-pot synthetic protocols...

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Xia XF, Shu XZ, Ji KG, et al. Platinum-catalyzed Michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of alpha,beta-sp3 C-H bonds. J Org Chem. 2010;75(9):2893-902doi: 10.1021/jo100133z.
Xia, X. F., Shu, X. Z., Ji, K. G., Yang, Y. F., Ali, S., Shaukat, A., Liu, X. Y., & Liang, Y. M. (2010). Platinum-catalyzed Michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of alpha,beta-sp3 C-H bonds. The Journal of organic chemistry, 75(9), 2893-902. https://doi.org/10.1021/jo100133z
Xia, Xiao-Feng, et al. "Platinum-catalyzed Michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of alpha,beta-sp3 C-H bonds." The Journal of organic chemistry vol. 75,9 (2010): 2893-902. doi: https://doi.org/10.1021/jo100133z
Xia XF, Shu XZ, Ji KG, Yang YF, Ali S, Shaukat A, Liu XY, Liang YM. Platinum-catalyzed Michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of alpha,beta-sp3 C-H bonds. J Org Chem. 2010 May 07;75(9):2893-902. doi: 10.1021/jo100133z. PMID: 20345090.
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Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones.

Beilstein journal of organic chemistry

Brice H, Clayden J, Hamilton SD.
PMID: 20502604
Beilstein J Org Chem. 2010 Mar 02;6:22. doi: 10.3762/bjoc.6.22.

The silyl enol ether derivatives of ketones or esters tethered by a hydrocarbon or ether linkage to the 3-position of a pyridine ring undergo dearomatising nucleophilic attack on the ring once it is activated (as an acylpyridinium species) by...

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Brice H, Clayden J, Hamilton SD. Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones. Beilstein J Org Chem. 2010;6:22doi: 10.3762/bjoc.6.22.
Brice, H., Clayden, J., & Hamilton, S. D. (2010). Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones. Beilstein journal of organic chemistry, 622. https://doi.org/10.3762/bjoc.6.22
Brice, Heloise, et al. "Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones." Beilstein journal of organic chemistry vol. 6 (2010): 22. doi: https://doi.org/10.3762/bjoc.6.22
Brice H, Clayden J, Hamilton SD. Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones. Beilstein J Org Chem. 2010 Mar 02;6:22. doi: 10.3762/bjoc.6.22. PMID: 20502604; PMCID: PMC2874404.
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New piperidine scaffolds via nucleophilic reactivity of (-)-phenyloxazolopiperidine.

The Journal of organic chemistry

Poupon E, François D, Kunesch N, Husson HP.
PMID: 15153016
J Org Chem. 2004 May 28;69(11):3836-41. doi: 10.1021/jo0499524.

The present work illustrates the power of compound 2 as a chiral, nonracemic, and stable 2-piperideine (enamine) equivalent in the rapid and efficient construction of 3-substituted piperidines (carbon-carbon and carbon-sulfur bonds) such as 3-spiropiperidines. This methodology offers a new...

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Poupon E, François D, Kunesch N, et al. New piperidine scaffolds via nucleophilic reactivity of (-)-phenyloxazolopiperidine. J Org Chem. 2004;69(11):3836-41doi: 10.1021/jo0499524.
Poupon, E., François, D., Kunesch, N., & Husson, H. P. (2004). New piperidine scaffolds via nucleophilic reactivity of (-)-phenyloxazolopiperidine. The Journal of organic chemistry, 69(11), 3836-41. https://doi.org/10.1021/jo0499524
Poupon, Erwan, et al. "New piperidine scaffolds via nucleophilic reactivity of (-)-phenyloxazolopiperidine." The Journal of organic chemistry vol. 69,11 (2004): 3836-41. doi: https://doi.org/10.1021/jo0499524
Poupon E, François D, Kunesch N, Husson HP. New piperidine scaffolds via nucleophilic reactivity of (-)-phenyloxazolopiperidine. J Org Chem. 2004 May 28;69(11):3836-41. doi: 10.1021/jo0499524. PMID: 15153016.
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Showing 13 to 24 of 236 entries