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Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening.

Organic letters

Han H, Bae I, Yoo EJ, Lee J, Do Y, Chang S.
PMID: 15496111
Org Lett. 2004 Oct 28;6(22):4109-12. doi: 10.1021/ol0481784.

[reaction: see text] We have developed, on the basis of a chelation-strategy, an efficient copper-catalyzed aziridination protocol with the use of 5-methyl-2-pyridinesulfonamide and PhI(OAc)(2). The reaction proceeds smoothly under mild conditions to give aziridines in moderate to good yields...

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Han H, Bae I, Yoo EJ, et al. Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening. Org Lett. 2004;6(22):4109-12doi: 10.1021/ol0481784.
Han, H., Bae, I., Yoo, E. J., Lee, J., Do, Y., & Chang, S. (2004). Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening. Organic letters, 6(22), 4109-12. https://doi.org/10.1021/ol0481784
Han, Hoon, et al. "Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening." Organic letters vol. 6,22 (2004): 4109-12. doi: https://doi.org/10.1021/ol0481784
Han H, Bae I, Yoo EJ, Lee J, Do Y, Chang S. Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening. Org Lett. 2004 Oct 28;6(22):4109-12. doi: 10.1021/ol0481784. PMID: 15496111.
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The control of the nitrogen inversion in alkyl-substituted diaziridines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Trapp O, Schurig V, Kostyanovsky RG.
PMID: 14978821
Chemistry. 2004 Feb 20;10(4):951-7. doi: 10.1002/chem.200305494.

For the first time the nitrogen inversion barriers in 3,3-unsubstituted trans-diaziridines, such as 1,2-di-tert-butyldiaziridine (1) and 1,2-di-n-butyldiaziridine (2) were determined. Enantioselective stopped-flow multidimensional gas chromatography was used to investigate the enantiomerization barrier of 1 between 126.2 and 171.0 degrees...

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Trapp O, Schurig V, Kostyanovsky RG. The control of the nitrogen inversion in alkyl-substituted diaziridines. Chemistry. 2004;10(4):951-7doi: 10.1002/chem.200305494.
Trapp, O., Schurig, V., & Kostyanovsky, R. G. (2004). The control of the nitrogen inversion in alkyl-substituted diaziridines. Chemistry (Weinheim an der Bergstrasse, Germany), 10(4), 951-7. https://doi.org/10.1002/chem.200305494
Trapp, O, et al. "The control of the nitrogen inversion in alkyl-substituted diaziridines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 10,4 (2004): 951-7. doi: https://doi.org/10.1002/chem.200305494
Trapp O, Schurig V, Kostyanovsky RG. The control of the nitrogen inversion in alkyl-substituted diaziridines. Chemistry. 2004 Feb 20;10(4):951-7. doi: 10.1002/chem.200305494. PMID: 14978821.
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A general process for the haloamidation of olefins. Scope and mechanism.

Journal of the American Chemical Society

Yeung YY, Gao X, Corey EJ.
PMID: 16866514
J Am Chem Soc. 2006 Aug 02;128(30):9644-5. doi: 10.1021/ja063675w.

A methodology is described for the addition of a bromine atom and an amide nitrogen in a trans sense to an olefinic double bond. The process, which is illustrated by numerous examples, involves the use of an N-bromoamide and...

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Yeung YY, Gao X, Corey EJ. A general process for the haloamidation of olefins. Scope and mechanism. J Am Chem Soc. 2006;128(30):9644-5doi: 10.1021/ja063675w.
Yeung, Y. Y., Gao, X., & Corey, E. J. (2006). A general process for the haloamidation of olefins. Scope and mechanism. Journal of the American Chemical Society, 128(30), 9644-5. https://doi.org/10.1021/ja063675w
Yeung, Ying-Yeung, et al. "A general process for the haloamidation of olefins. Scope and mechanism." Journal of the American Chemical Society vol. 128,30 (2006): 9644-5. doi: https://doi.org/10.1021/ja063675w
Yeung YY, Gao X, Corey EJ. A general process for the haloamidation of olefins. Scope and mechanism. J Am Chem Soc. 2006 Aug 02;128(30):9644-5. doi: 10.1021/ja063675w. PMID: 16866514.
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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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A new multicomponent reaction catalyzed by a [Lewis Acid](+)[Co(CO)(4)](-) catalyst: stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO.

Journal of the American Chemical Society

Church TL, Byrne CM, Lobkovsky EB, Coates GW.
PMID: 17564443
J Am Chem Soc. 2007 Jul 04;129(26):8156-62. doi: 10.1021/ja069065d. Epub 2007 Jun 12.

The use of mechanistic information to develop a new, catalytic multicomponent reaction is described. The complex [(salph)Al(THF)2]+[Co(CO)4]- (1, salph = N,N'-o-phenylenebis(3,5-di-tert-butylsalicylideneimine), THF = tetrahydrofuran), which is known to carbonylate epoxides, aziridines, and beta-lactones, was used to catalyze the synthesis...

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Church TL, Byrne CM, Lobkovsky EB, et al. A new multicomponent reaction catalyzed by a [Lewis Acid](+)[Co(CO)(4)](-) catalyst: stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. J Am Chem Soc. 2007;129(26):8156-62doi: 10.1021/ja069065d.
Church, T. L., Byrne, C. M., Lobkovsky, E. B., & Coates, G. W. (2007). A new multicomponent reaction catalyzed by a [Lewis Acid](+)[Co(CO)(4)](-) catalyst: stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. Journal of the American Chemical Society, 129(26), 8156-62. https://doi.org/10.1021/ja069065d
Church, Tamara L, et al. "A new multicomponent reaction catalyzed by a [Lewis Acid](+)[Co(CO)(4)](-) catalyst: stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO." Journal of the American Chemical Society vol. 129,26 (2007): 8156-62. doi: https://doi.org/10.1021/ja069065d
Church TL, Byrne CM, Lobkovsky EB, Coates GW. A new multicomponent reaction catalyzed by a [Lewis Acid](+)[Co(CO)(4)](-) catalyst: stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. J Am Chem Soc. 2007 Jul 04;129(26):8156-62. doi: 10.1021/ja069065d. Epub 2007 Jun 12. PMID: 17564443.
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Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes.

Organometallics

Blum SA, Rivera VA, Ruck RT, Michael FE, Bergman RG.
PMID: 16508693
Organometallics. 2005 Mar 28;24(7):1647-1659. doi: 10.1021/om049105r.

The reactions of the bis(cyclopentadienyl)(tert-butylimido)zirconium complex (Cp(2)Zr=N-t-Bu)(THF) (1) with epoxides, aziridines, and episulfides were investigated. Heterocycles without accessible beta-hydrogens undergo insertion/protonation of the C-X bond to produce 1,2-amino alcohols (X = O) and 1,2-diamines (X = NR), whereas heterocycles...

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Blum SA, Rivera VA, Ruck RT, et al. Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes. Organometallics. 2005;24(7):1647-1659doi: 10.1021/om049105r.
Blum, S. A., Rivera, V. A., Ruck, R. T., Michael, F. E., & Bergman, R. G. (2005). Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes. Organometallics, 24(7), 1647-1659. https://doi.org/10.1021/om049105r
Blum, Suzanne A, et al. "Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes." Organometallics vol. 24,7 (2005): 1647-1659. doi: https://doi.org/10.1021/om049105r
Blum SA, Rivera VA, Ruck RT, Michael FE, Bergman RG. Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes. Organometallics. 2005 Mar 28;24(7):1647-1659. doi: 10.1021/om049105r. PMID: 16508693; PMCID: PMC1383653.
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A new, mild synthesis of N-sulfonyl ketimines via the palladium-catalyzed isomerization of aziridines.

Organic letters

Wolfe JP, Ney JE.
PMID: 14627395
Org Lett. 2003 Nov 27;5(24):4607-10. doi: 10.1021/ol0357651.

[reaction: see text] A new method for the synthesis of N-tosylketimines via the palladium-catalyzed isomerization of N-tosylaziridines is described. The mild reaction conditions tolerate the presence of a variety of functional groups including ketones, esters, and acetals. The reactions...

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Wolfe JP, Ney JE. A new, mild synthesis of N-sulfonyl ketimines via the palladium-catalyzed isomerization of aziridines. Org Lett. 2003;5(24):4607-10doi: 10.1021/ol0357651.
Wolfe, J. P., & Ney, J. E. (2003). A new, mild synthesis of N-sulfonyl ketimines via the palladium-catalyzed isomerization of aziridines. Organic letters, 5(24), 4607-10. https://doi.org/10.1021/ol0357651
Wolfe, John P, and Ney, Joshua E. "A new, mild synthesis of N-sulfonyl ketimines via the palladium-catalyzed isomerization of aziridines." Organic letters vol. 5,24 (2003): 4607-10. doi: https://doi.org/10.1021/ol0357651
Wolfe JP, Ney JE. A new, mild synthesis of N-sulfonyl ketimines via the palladium-catalyzed isomerization of aziridines. Org Lett. 2003 Nov 27;5(24):4607-10. doi: 10.1021/ol0357651. PMID: 14627395.
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Construction of three contiguous tertiary stereocenters from aziridines in one step.

Organic letters

Blyumin EV, Gallon HJ, Yudin AK.
PMID: 17929932
Org Lett. 2007 Nov 08;9(23):4677-80. doi: 10.1021/ol7015302. Epub 2007 Oct 12.

A range of active methylene nucleophiles were found to participate in ring-opening of tosylated aziridines under mild phase-transfer catalyzed conditions. High isolated yields coupled with a 1:1 reaction stoichiometry and high levels of relative stereocontrol are distinguishing features of...

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Blyumin EV, Gallon HJ, Yudin AK. Construction of three contiguous tertiary stereocenters from aziridines in one step. Org Lett. 2007;9(23):4677-80doi: 10.1021/ol7015302.
Blyumin, E. V., Gallon, H. J., & Yudin, A. K. (2007). Construction of three contiguous tertiary stereocenters from aziridines in one step. Organic letters, 9(23), 4677-80. https://doi.org/10.1021/ol7015302
Blyumin, Evgeniy V, et al. "Construction of three contiguous tertiary stereocenters from aziridines in one step." Organic letters vol. 9,23 (2007): 4677-80. doi: https://doi.org/10.1021/ol7015302
Blyumin EV, Gallon HJ, Yudin AK. Construction of three contiguous tertiary stereocenters from aziridines in one step. Org Lett. 2007 Nov 08;9(23):4677-80. doi: 10.1021/ol7015302. Epub 2007 Oct 12. PMID: 17929932.
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Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions.

Chemical communications (Cambridge, England)

Carballares S, Craig D, Hyland CJ, Lu P, Mathie T, White AJ.
PMID: 19137182
Chem Commun (Camb). 2009 Jan 28;(4):451-3. doi: 10.1039/b815971h. Epub 2008 Nov 26.

The highly regioselective, stereospecific ring-opening of trisubstituted N-tosylaziridines possessing vinyl and hydroxymethyl groups by sulfone- and sulfide-stablised carbanions is reported.

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Carballares S, Craig D, Hyland CJ, et al. Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions. Chem Commun (Camb). 2008;(4):451-3doi: 10.1039/b815971h.
Carballares, S., Craig, D., Hyland, C. J., Lu, P., Mathie, T., & White, A. J. (2009). Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions. Chemical communications (Cambridge, England), (4), 451-3. https://doi.org/10.1039/b815971h
Carballares, Santiago, et al. "Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions." Chemical communications (Cambridge, England) vol. ,4 (2009): 451-3. doi: https://doi.org/10.1039/b815971h
Carballares S, Craig D, Hyland CJ, Lu P, Mathie T, White AJ. Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions. Chem Commun (Camb). 2009 Jan 28;(4):451-3. doi: 10.1039/b815971h. Epub 2008 Nov 26. PMID: 19137182.
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Catalytic, enantioselective ring opening of aziridines.

Angewandte Chemie (International ed. in English)

Schneider C.
PMID: 19173352
Angew Chem Int Ed Engl. 2009;48(12):2082-4. doi: 10.1002/anie.200805542.

Cooperative metal centers in a bimetallic catalyst facilitate the highly enantioselective ring opening of meso aziridines 1 with silyl nucleophiles (see scheme; TMS = trimethylsilyl). The 1,2-azidoamides 2 and 1,2-amidonitriles 3 obtained in this way in high yields and...

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Schneider C. Catalytic, enantioselective ring opening of aziridines. Angew Chem Int Ed Engl. 2009;48(12):2082-4doi: 10.1002/anie.200805542.
Schneider, C. (2009). Catalytic, enantioselective ring opening of aziridines. Angewandte Chemie (International ed. in English), 48(12), 2082-4. https://doi.org/10.1002/anie.200805542
Schneider, Christoph. "Catalytic, enantioselective ring opening of aziridines." Angewandte Chemie (International ed. in English) vol. 48,12 (2009): 2082-4. doi: https://doi.org/10.1002/anie.200805542
Schneider C. Catalytic, enantioselective ring opening of aziridines. Angew Chem Int Ed Engl. 2009;48(12):2082-4. doi: 10.1002/anie.200805542. PMID: 19173352.
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Addition reactions of chloro- or iodomethyllithium to imines. Synthesis of enantiopure aziridines and beta-chloroamines.

The Journal of organic chemistry

Concellón JM, Rodríguez-Solla H, Bernad PL, Simal C.
PMID: 19222246
J Org Chem. 2009 Mar 20;74(6):2452-9. doi: 10.1021/jo802596y.

We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodo- or chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment...

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Concellón JM, Rodríguez-Solla H, Bernad PL, et al. Addition reactions of chloro- or iodomethyllithium to imines. Synthesis of enantiopure aziridines and beta-chloroamines. J Org Chem. 2009;74(6):2452-9doi: 10.1021/jo802596y.
Concellón, J. M., Rodríguez-Solla, H., Bernad, P. L., & Simal, C. (2009). Addition reactions of chloro- or iodomethyllithium to imines. Synthesis of enantiopure aziridines and beta-chloroamines. The Journal of organic chemistry, 74(6), 2452-9. https://doi.org/10.1021/jo802596y
Concellón, José M, et al. "Addition reactions of chloro- or iodomethyllithium to imines. Synthesis of enantiopure aziridines and beta-chloroamines." The Journal of organic chemistry vol. 74,6 (2009): 2452-9. doi: https://doi.org/10.1021/jo802596y
Concellón JM, Rodríguez-Solla H, Bernad PL, Simal C. Addition reactions of chloro- or iodomethyllithium to imines. Synthesis of enantiopure aziridines and beta-chloroamines. J Org Chem. 2009 Mar 20;74(6):2452-9. doi: 10.1021/jo802596y. PMID: 19222246.
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Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles.

The Journal of organic chemistry

Wang Z, Cui YT, Xu ZB, Qu J.
PMID: 18288864
J Org Chem. 2008 Mar 21;73(6):2270-4. doi: 10.1021/jo702401t. Epub 2008 Feb 21.

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 degrees C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot...

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Wang Z, Cui YT, Xu ZB, et al. Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles. J Org Chem. 2008;73(6):2270-4doi: 10.1021/jo702401t.
Wang, Z., Cui, Y. T., Xu, Z. B., & Qu, J. (2008). Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles. The Journal of organic chemistry, 73(6), 2270-4. https://doi.org/10.1021/jo702401t
Wang, Zhi, et al. "Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles." The Journal of organic chemistry vol. 73,6 (2008): 2270-4. doi: https://doi.org/10.1021/jo702401t
Wang Z, Cui YT, Xu ZB, Qu J. Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles. J Org Chem. 2008 Mar 21;73(6):2270-4. doi: 10.1021/jo702401t. Epub 2008 Feb 21. PMID: 18288864.
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Showing 25 to 36 of 448 entries