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Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry(1).

The Journal of organic chemistry

Pepito AS, Dittmer DC.
PMID: 11671893
J Org Chem. 1997 Nov 14;62(23):7920-7925. doi: 10.1021/jo962024n.

Sulfonate esters of aziridinemethanols are converted to allylic amines by treatment with telluride ion obtained by reduction of elemental tellurium. In the course of the reaction, tellurium(0) is reformed and may be reused, thus removing the need to dispose...

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Pepito AS, Dittmer DC. Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry(1). J Org Chem. 1997;62(23):7920-7925doi: 10.1021/jo962024n.
Pepito, A. S., & Dittmer, D. C. (1997). Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry(1). The Journal of organic chemistry, 62(23), 7920-7925. https://doi.org/10.1021/jo962024n
Pepito, Aurora S., and Dittmer, Donald C.. "Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry(1)." The Journal of organic chemistry vol. 62,23 (1997): 7920-7925. doi: https://doi.org/10.1021/jo962024n
Pepito AS, Dittmer DC. Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry(1). J Org Chem. 1997 Nov 14;62(23):7920-7925. doi: 10.1021/jo962024n. PMID: 11671893.
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Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (Z)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange: Stereoselective Synthesis of 2-Acylaziridines.

The Journal of organic chemistry

Ochiai M, Kitagawa Y.
PMID: 11674419
J Org Chem. 1999 Apr 30;64(9):3181-3189. doi: 10.1021/jo982346m.

Monocarbonyl iodonium ylides, generated in situ from (Z)-(2-acetoxyvinyl)iodonium salts via an ester exchange reaction with EtOLi, undergo alkylidene transfer reactions to activated imines yielding 2-acylaziridines in good yields. The stereochemical outcome of this aziridination was shown to be dependent...

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Ochiai M, Kitagawa Y. Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (Z)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange: Stereoselective Synthesis of 2-Acylaziridines. J Org Chem. 1999;64(9):3181-3189doi: 10.1021/jo982346m.
Ochiai, M., & Kitagawa, Y. (1999). Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (Z)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange: Stereoselective Synthesis of 2-Acylaziridines. The Journal of organic chemistry, 64(9), 3181-3189. https://doi.org/10.1021/jo982346m
Ochiai, Masahito, and Kitagawa, Yutaka. "Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (Z)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange: Stereoselective Synthesis of 2-Acylaziridines." The Journal of organic chemistry vol. 64,9 (1999): 3181-3189. doi: https://doi.org/10.1021/jo982346m
Ochiai M, Kitagawa Y. Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (Z)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange: Stereoselective Synthesis of 2-Acylaziridines. J Org Chem. 1999 Apr 30;64(9):3181-3189. doi: 10.1021/jo982346m. PMID: 11674419.
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Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening.

The Journal of organic chemistry

Bergmeier SC, Stanchina DM.
PMID: 11671773
J Org Chem. 1997 Jun 27;62(13):4449-4456. doi: 10.1021/jo970473x.

A facile synthesis of differently substituted vicinal amino alcohols is reported. We have demonstrated that these amino alcohols could be readily prepared from the oxazolidinones by treatment with aqueous base. We have synthesized a variety of substituted bicyclic aziridine...

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Bergmeier SC, Stanchina DM. Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening. J Org Chem. 1997;62(13):4449-4456doi: 10.1021/jo970473x.
Bergmeier, S. C., & Stanchina, D. M. (1997). Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening. The Journal of organic chemistry, 62(13), 4449-4456. https://doi.org/10.1021/jo970473x
Bergmeier, Stephen C., and Stanchina, Dionne M.. "Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening." The Journal of organic chemistry vol. 62,13 (1997): 4449-4456. doi: https://doi.org/10.1021/jo970473x
Bergmeier SC, Stanchina DM. Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening. J Org Chem. 1997 Jun 27;62(13):4449-4456. doi: 10.1021/jo970473x. PMID: 11671773.
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Effective ring-opening reaction of aziridines with trimethylsilyl compounds: A facile access to beta-amino acids and 1,2-diamine derivatives.

The Journal of organic chemistry

Wu J, Hou XL, Dai LX.
PMID: 10814094
J Org Chem. 2000 Mar 10;65(5):1344-8. doi: 10.1021/jo9913816.

Ring-opening reactions of aziridines with trimethylsilyl compounds triggered by tetrabutylammonium fluoride give the corresponding products regioselectively in excellent yield. It provides a facile and efficient procedure for the ring-opening reactions of aziridines and affords a practical access to the...

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Wu J, Hou XL, Dai LX. Effective ring-opening reaction of aziridines with trimethylsilyl compounds: A facile access to beta-amino acids and 1,2-diamine derivatives. J Org Chem. 2000;65(5):1344-8doi: 10.1021/jo9913816.
Wu, J., Hou, X. L., & Dai, L. X. (2000). Effective ring-opening reaction of aziridines with trimethylsilyl compounds: A facile access to beta-amino acids and 1,2-diamine derivatives. The Journal of organic chemistry, 65(5), 1344-8. https://doi.org/10.1021/jo9913816
Wu, et al. "Effective ring-opening reaction of aziridines with trimethylsilyl compounds: A facile access to beta-amino acids and 1,2-diamine derivatives." The Journal of organic chemistry vol. 65,5 (2000): 1344-8. doi: https://doi.org/10.1021/jo9913816
Wu J, Hou XL, Dai LX. Effective ring-opening reaction of aziridines with trimethylsilyl compounds: A facile access to beta-amino acids and 1,2-diamine derivatives. J Org Chem. 2000 Mar 10;65(5):1344-8. doi: 10.1021/jo9913816. PMID: 10814094.
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The effect of HMPA on the reactivity of epoxides, aziridines, and alkyl halides with organolithium reagents.

Journal of the American Chemical Society

Reich HJ, Sanders AW, Fiedler AT, Bevan MJ.
PMID: 12418882
J Am Chem Soc. 2002 Nov 13;124(45):13386-7. doi: 10.1021/ja026915q.

A kinetic study of the effect of added HMPA cosolvent on the reaction of 2-lithio-1,3-dithiane (1), bis(phenylthio)methyllithium (2), and bis(3,5-bistrifluoromethylphenylthio)methyllithium (3) with methyloxirane (propylene oxide), N-tosyl-2-methylaziridine, and the several alkyl halides (BuCl, BuBr, BuI, allyl chloride) was carried out....

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Reich HJ, Sanders AW, Fiedler AT, et al. The effect of HMPA on the reactivity of epoxides, aziridines, and alkyl halides with organolithium reagents. J Am Chem Soc. 2002;124(45):13386-7doi: 10.1021/ja026915q.
Reich, H. J., Sanders, A. W., Fiedler, A. T., & Bevan, M. J. (2002). The effect of HMPA on the reactivity of epoxides, aziridines, and alkyl halides with organolithium reagents. Journal of the American Chemical Society, 124(45), 13386-7. https://doi.org/10.1021/ja026915q
Reich, Hans J, et al. "The effect of HMPA on the reactivity of epoxides, aziridines, and alkyl halides with organolithium reagents." Journal of the American Chemical Society vol. 124,45 (2002): 13386-7. doi: https://doi.org/10.1021/ja026915q
Reich HJ, Sanders AW, Fiedler AT, Bevan MJ. The effect of HMPA on the reactivity of epoxides, aziridines, and alkyl halides with organolithium reagents. J Am Chem Soc. 2002 Nov 13;124(45):13386-7. doi: 10.1021/ja026915q. PMID: 12418882.
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2-ethynylaziridines as chiral carbon nucleophiles: stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group.

The Journal of organic chemistry

Ohno H, Hamaguchi H, Tanaka T.
PMID: 11262139
J Org Chem. 2001 Mar 09;66(5):1867-75. doi: 10.1021/jo005756v.

Allenylindium reagents bearing a protected amino group were effectively prepared from N-protected 3-alkyl-2-ethynylaziridines by treatment with InI in the presence of Pd(PPh(3))(4) and H(2)O. Stereoselective addition of the allenylindium to aliphatic or aromatic aldehydes affords 1,3-amino alcohols bearing three...

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Ohno H, Hamaguchi H, Tanaka T. 2-ethynylaziridines as chiral carbon nucleophiles: stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group. J Org Chem. 2001;66(5):1867-75doi: 10.1021/jo005756v.
Ohno, H., Hamaguchi, H., & Tanaka, T. (2001). 2-ethynylaziridines as chiral carbon nucleophiles: stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group. The Journal of organic chemistry, 66(5), 1867-75. https://doi.org/10.1021/jo005756v
Ohno, H, et al. "2-ethynylaziridines as chiral carbon nucleophiles: stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group." The Journal of organic chemistry vol. 66,5 (2001): 1867-75. doi: https://doi.org/10.1021/jo005756v
Ohno H, Hamaguchi H, Tanaka T. 2-ethynylaziridines as chiral carbon nucleophiles: stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group. J Org Chem. 2001 Mar 09;66(5):1867-75. doi: 10.1021/jo005756v. PMID: 11262139.
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Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines.

The Journal of organic chemistry

Li BF, Yuan K, Zhang MJ, Wu H, Dai LX, Wang QR, Hou XL.
PMID: 12895059
J Org Chem. 2003 Aug 08;68(16):6264-7. doi: 10.1021/jo034477f.

The reaction of chiral sulfinimines 1c-g derived from aliphatic aldehydes with TMSCN in the presence of CsF gave alpha-amino nitriles in high diastereoselectivity and yield. alpha,beta-Diamino acid derivatives were also obtained in high diastereoselectivity from the reaction of 2-aziridinesulfinimines...

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Li BF, Yuan K, Zhang MJ, et al. Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines. J Org Chem. 2003;68(16):6264-7doi: 10.1021/jo034477f.
Li, B. F., Yuan, K., Zhang, M. J., Wu, H., Dai, L. X., Wang, Q. R., & Hou, X. L. (2003). Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines. The Journal of organic chemistry, 68(16), 6264-7. https://doi.org/10.1021/jo034477f
Li, Bin-Feng, et al. "Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines." The Journal of organic chemistry vol. 68,16 (2003): 6264-7. doi: https://doi.org/10.1021/jo034477f
Li BF, Yuan K, Zhang MJ, Wu H, Dai LX, Wang QR, Hou XL. Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines. J Org Chem. 2003 Aug 08;68(16):6264-7. doi: 10.1021/jo034477f. PMID: 12895059.
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Carbonylative ring expansion of aziridines to beta-lactams with rhodium-complexed dendrimers on a resin.

The Journal of organic chemistry

Lu SM, Alper H.
PMID: 15132571
J Org Chem. 2004 May 14;69(10):3558-61. doi: 10.1021/jo030353r.

Rhodium-complexed dendrimers, supported on a resin, were evaluated as catalysts for the carbonylative ring expansion reactions of a variety of aziridines with carbon monoxide to give beta-lactams. The effects of reaction temperature, solvent, time, and pressure of carbon monoxide...

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Lu SM, Alper H. Carbonylative ring expansion of aziridines to beta-lactams with rhodium-complexed dendrimers on a resin. J Org Chem. 2004;69(10):3558-61doi: 10.1021/jo030353r.
Lu, S. M., & Alper, H. (2004). Carbonylative ring expansion of aziridines to beta-lactams with rhodium-complexed dendrimers on a resin. The Journal of organic chemistry, 69(10), 3558-61. https://doi.org/10.1021/jo030353r
Lu, Shui-Ming, and Alper, Howard. "Carbonylative ring expansion of aziridines to beta-lactams with rhodium-complexed dendrimers on a resin." The Journal of organic chemistry vol. 69,10 (2004): 3558-61. doi: https://doi.org/10.1021/jo030353r
Lu SM, Alper H. Carbonylative ring expansion of aziridines to beta-lactams with rhodium-complexed dendrimers on a resin. J Org Chem. 2004 May 14;69(10):3558-61. doi: 10.1021/jo030353r. PMID: 15132571.
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Highly selective oxidative cleavage of beta-cyclodextrin-epoxide/aziridine complexes with IBX in water.

The Journal of organic chemistry

Surendra K, Krishnaveni NS, Reddy MA, Nageswar YV, Rao KR.
PMID: 14604392
J Org Chem. 2003 Nov 14;68(23):9119-21. doi: 10.1021/jo034079c.

Water, an environmentally friendly reaction medium, has been utilized for the reaction of IBX with various epoxides 1 and aziridines 2 as their beta-cyclodextrin complexes to afford for the first time alpha-hydroxyketones 3 and alpha-aminoketones 4, respectively.

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Surendra K, Krishnaveni NS, Reddy MA, et al. Highly selective oxidative cleavage of beta-cyclodextrin-epoxide/aziridine complexes with IBX in water. J Org Chem. 2003;68(23):9119-21doi: 10.1021/jo034079c.
Surendra, K., Krishnaveni, N. S., Reddy, M. A., Nageswar, Y. V., & Rao, K. R. (2003). Highly selective oxidative cleavage of beta-cyclodextrin-epoxide/aziridine complexes with IBX in water. The Journal of organic chemistry, 68(23), 9119-21. https://doi.org/10.1021/jo034079c
Surendra, K, et al. "Highly selective oxidative cleavage of beta-cyclodextrin-epoxide/aziridine complexes with IBX in water." The Journal of organic chemistry vol. 68,23 (2003): 9119-21. doi: https://doi.org/10.1021/jo034079c
Surendra K, Krishnaveni NS, Reddy MA, Nageswar YV, Rao KR. Highly selective oxidative cleavage of beta-cyclodextrin-epoxide/aziridine complexes with IBX in water. J Org Chem. 2003 Nov 14;68(23):9119-21. doi: 10.1021/jo034079c. PMID: 14604392.
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Stereoselective aziridination of cyclic allylic alcohols using chloramine-T.

Organic & biomolecular chemistry

Coote SC, O'Brien P, Whitwood AC.
PMID: 19005588
Org Biomol Chem. 2008 Dec 07;6(23):4299-314. doi: 10.1039/b811137e. Epub 2008 Oct 08.

The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC(6)H(4)SO(2)NClNa, TsNClNa and t-BuSO(2)NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and...

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Coote SC, O'Brien P, Whitwood AC. Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. Org Biomol Chem. 2008;6(23):4299-314doi: 10.1039/b811137e.
Coote, S. C., O'Brien, P., & Whitwood, A. C. (2008). Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. Organic & biomolecular chemistry, 6(23), 4299-314. https://doi.org/10.1039/b811137e
Coote, Susannah C, et al. "Stereoselective aziridination of cyclic allylic alcohols using chloramine-T." Organic & biomolecular chemistry vol. 6,23 (2008): 4299-314. doi: https://doi.org/10.1039/b811137e
Coote SC, O'Brien P, Whitwood AC. Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. Org Biomol Chem. 2008 Dec 07;6(23):4299-314. doi: 10.1039/b811137e. Epub 2008 Oct 08. PMID: 19005588.
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Synthesis and reactivity of azapalladacyclobutanes.

Journal of the American Chemical Society

Ney JE, Wolfe JP.
PMID: 17132008
J Am Chem Soc. 2006 Dec 06;128(48):15415-22. doi: 10.1021/ja0660756.

N-Sulfonyl aziridines undergo oxidative addition to palladium(0) complexes generated in situ from mixtures of Pd2(dba)3 and 1,10-phenanthroline. The resulting azapalladacyclobutane complexes undergo intramolecular carbopalladation in the presence of copper(I) iodide to afford azapalladabicyclo[3.2.1]octanes. A deuterium-labeling experiment indicates that the...

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Ney JE, Wolfe JP. Synthesis and reactivity of azapalladacyclobutanes. J Am Chem Soc. 2006;128(48):15415-22doi: 10.1021/ja0660756.
Ney, J. E., & Wolfe, J. P. (2006). Synthesis and reactivity of azapalladacyclobutanes. Journal of the American Chemical Society, 128(48), 15415-22. https://doi.org/10.1021/ja0660756
Ney, Joshua E, and Wolfe, John P. "Synthesis and reactivity of azapalladacyclobutanes." Journal of the American Chemical Society vol. 128,48 (2006): 15415-22. doi: https://doi.org/10.1021/ja0660756
Ney JE, Wolfe JP. Synthesis and reactivity of azapalladacyclobutanes. J Am Chem Soc. 2006 Dec 06;128(48):15415-22. doi: 10.1021/ja0660756. PMID: 17132008.
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The Brønsted acid-catalyzed direct aza-Darzens synthesis of N-alkyl cis-aziridines.

Journal of the American Chemical Society

Williams AL, Johnston JN.
PMID: 14871074
J Am Chem Soc. 2004 Feb 18;126(6):1612-3. doi: 10.1021/ja0385282.

A mild protocol for the synthesis of cis-aziridines is described that employs a catalytic amount of Brønsted acid. Despite the potential for diazo compound decomposition via alkylation or homocoupling upon exposure to a proton source, these pathways are slow...

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Williams AL, Johnston JN. The Brønsted acid-catalyzed direct aza-Darzens synthesis of N-alkyl cis-aziridines. J Am Chem Soc. 2004;126(6):1612-3doi: 10.1021/ja0385282.
Williams, A. L., & Johnston, J. N. (2004). The Brønsted acid-catalyzed direct aza-Darzens synthesis of N-alkyl cis-aziridines. Journal of the American Chemical Society, 126(6), 1612-3. https://doi.org/10.1021/ja0385282
Williams, Amie L, and Johnston, Jeffrey N. "The Brønsted acid-catalyzed direct aza-Darzens synthesis of N-alkyl cis-aziridines." Journal of the American Chemical Society vol. 126,6 (2004): 1612-3. doi: https://doi.org/10.1021/ja0385282
Williams AL, Johnston JN. The Brønsted acid-catalyzed direct aza-Darzens synthesis of N-alkyl cis-aziridines. J Am Chem Soc. 2004 Feb 18;126(6):1612-3. doi: 10.1021/ja0385282. PMID: 14871074.
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Showing 13 to 24 of 448 entries