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Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides.

Organic & biomolecular chemistry

Muthusamy S, Kumar SG.
PMID: 26786749
Org Biomol Chem. 2016 Feb 21;14(7):2228-40. doi: 10.1039/c5ob02322j. Epub 2016 Jan 20.

Investigations of regio-, chemo- and diastereoselective studies on three- as well as four-component reactions using diazooxindoles, imines, aldehydes, amines, alkenes, alkynes or diazenes in the presence of copper(I) thiophene-2-carboxylate are performed to furnish spiroindolo-pyrrolidine/-imidazolidine/-triazolidine ring systems in good yields....

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Muthusamy S, Kumar SG. Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides. Org Biomol Chem. 2016;14(7):2228-40doi: 10.1039/c5ob02322j.
Muthusamy, S., & Kumar, S. G. (2016). Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides. Organic & biomolecular chemistry, 14(7), 2228-40. https://doi.org/10.1039/c5ob02322j
Muthusamy, Sengodagounder, and Kumar, Singaravelan Ganesh. "Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides." Organic & biomolecular chemistry vol. 14,7 (2016): 2228-40. doi: https://doi.org/10.1039/c5ob02322j
Muthusamy S, Kumar SG. Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides. Org Biomol Chem. 2016 Feb 21;14(7):2228-40. doi: 10.1039/c5ob02322j. Epub 2016 Jan 20. PMID: 26786749.
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Highly diastereoselective[3+2] cycloadditions between nonracemic p-tolysulfinimines and iminoesters: an efficient entry to enantiopure imidazolidines and vicinal diaminoalcohols.

Chemistry (Weinheim an der Bergstrasse, Germany)

Viso A, Férnandez de la Pradilla R, Garciá A, Guerro-Strachan C, Alonso M, Tortosa M, Flores A, Martínez-Ripoll M, Fonseca I, André I, Rodríguez A.
PMID: 12866563
Chemistry. 2003 Jun 16;9(12):2867-76. doi: 10.1002/chem.200204674.

A new procedure for the asymmetric synthesis of imidazolidines and vicinal diamines is reported. The 1,3-dipolar cycloaddition between nonracemic p-tolylsulfinimines and azomethine ylides generated in situ from alpha-iminoesters and LDA produces N-sulfinylimidazolidines with a high degree of stereocontrol. In...

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Viso A, Férnandez de la Pradilla R, Garciá A, et al. Highly diastereoselective[3+2] cycloadditions between nonracemic p-tolysulfinimines and iminoesters: an efficient entry to enantiopure imidazolidines and vicinal diaminoalcohols. Chemistry. 2003;9(12):2867-76doi: 10.1002/chem.200204674.
Viso, A., Férnandez de la Pradilla, R., Garciá, A., Guerro-Strachan, C., Alonso, M., Tortosa, M., Flores, A., Martínez-Ripoll, M., Fonseca, I., André, I., & Rodríguez, A. (2003). Highly diastereoselective[3+2] cycloadditions between nonracemic p-tolysulfinimines and iminoesters: an efficient entry to enantiopure imidazolidines and vicinal diaminoalcohols. Chemistry (Weinheim an der Bergstrasse, Germany), 9(12), 2867-76. https://doi.org/10.1002/chem.200204674
Viso, Alma, et al. "Highly diastereoselective[3+2] cycloadditions between nonracemic p-tolysulfinimines and iminoesters: an efficient entry to enantiopure imidazolidines and vicinal diaminoalcohols." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 9,12 (2003): 2867-76. doi: https://doi.org/10.1002/chem.200204674
Viso A, Férnandez de la Pradilla R, Garciá A, Guerro-Strachan C, Alonso M, Tortosa M, Flores A, Martínez-Ripoll M, Fonseca I, André I, Rodríguez A. Highly diastereoselective[3+2] cycloadditions between nonracemic p-tolysulfinimines and iminoesters: an efficient entry to enantiopure imidazolidines and vicinal diaminoalcohols. Chemistry. 2003 Jun 16;9(12):2867-76. doi: 10.1002/chem.200204674. PMID: 12866563.
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Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes.

The Journal of organic chemistry

Tarannum S, Sk S, Das S, Wani IA, Ghorai MK.
PMID: 31782305
J Org Chem. 2020 Jan 17;85(2):367-379. doi: 10.1021/acs.joc.9b02278. Epub 2019 Dec 13.

A mild one-pot stereospecific synthetic route to highly functionalized imidazolidines and oxazolidines via S

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Tarannum S, Sk S, Das S, et al. Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes. J Org Chem. 2019;85(2):367-379doi: 10.1021/acs.joc.9b02278.
Tarannum, S., Sk, S., Das, S., Wani, I. A., & Ghorai, M. K. (2020). Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes. The Journal of organic chemistry, 85(2), 367-379. https://doi.org/10.1021/acs.joc.9b02278
Tarannum, Saima, et al. "Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes." The Journal of organic chemistry vol. 85,2 (2020): 367-379. doi: https://doi.org/10.1021/acs.joc.9b02278
Tarannum S, Sk S, Das S, Wani IA, Ghorai MK. Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes. J Org Chem. 2020 Jan 17;85(2):367-379. doi: 10.1021/acs.joc.9b02278. Epub 2019 Dec 13. PMID: 31782305.
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Merging Imidazolidines with a Trifluoromethylated Tetrasubstituted Carbon through Tungsten Catalyzed 1,3-Dipolar Cycloaddition.

The Journal of organic chemistry

Chen Z, Zhou Y, Hu T, Xiong HY, Zhang G.
PMID: 34010567
J Org Chem. 2021 Jun 04;86(11):7714-7724. doi: 10.1021/acs.joc.1c00676. Epub 2021 May 19.

An unprecedented 1,3-dipole cycloaddition between acyclic CF

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Chen Z, Zhou Y, Hu T, et al. Merging Imidazolidines with a Trifluoromethylated Tetrasubstituted Carbon through Tungsten Catalyzed 1,3-Dipolar Cycloaddition. J Org Chem. 2021;86(11):7714-7724doi: 10.1021/acs.joc.1c00676.
Chen, Z., Zhou, Y., Hu, T., Xiong, H. Y., & Zhang, G. (2021). Merging Imidazolidines with a Trifluoromethylated Tetrasubstituted Carbon through Tungsten Catalyzed 1,3-Dipolar Cycloaddition. The Journal of organic chemistry, 86(11), 7714-7724. https://doi.org/10.1021/acs.joc.1c00676
Chen, Zhifang, et al. "Merging Imidazolidines with a Trifluoromethylated Tetrasubstituted Carbon through Tungsten Catalyzed 1,3-Dipolar Cycloaddition." The Journal of organic chemistry vol. 86,11 (2021): 7714-7724. doi: https://doi.org/10.1021/acs.joc.1c00676
Chen Z, Zhou Y, Hu T, Xiong HY, Zhang G. Merging Imidazolidines with a Trifluoromethylated Tetrasubstituted Carbon through Tungsten Catalyzed 1,3-Dipolar Cycloaddition. J Org Chem. 2021 Jun 04;86(11):7714-7724. doi: 10.1021/acs.joc.1c00676. Epub 2021 May 19. PMID: 34010567.
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A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes.

Organic letters

Golantsov NE, Golubenkova AS, Festa AA, Varlamov AV, Voskressensky LG.
PMID: 32484359
Org Lett. 2020 Jun 19;22(12):4726-4731. doi: 10.1021/acs.orglett.0c01530. Epub 2020 Jun 02.

The reaction of 1,2-disubstituted 2-imidazolines with electron-deficient alkynes proceeds as a pseudo-three-component process and forms imidazolidines with an

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Golantsov NE, Golubenkova AS, Festa AA, et al. A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes. Org Lett. 2020;22(12):4726-4731doi: 10.1021/acs.orglett.0c01530.
Golantsov, N. E., Golubenkova, A. S., Festa, A. A., Varlamov, A. V., & Voskressensky, L. G. (2020). A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes. Organic letters, 22(12), 4726-4731. https://doi.org/10.1021/acs.orglett.0c01530
Golantsov, Nikita E, et al. "A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes." Organic letters vol. 22,12 (2020): 4726-4731. doi: https://doi.org/10.1021/acs.orglett.0c01530
Golantsov NE, Golubenkova AS, Festa AA, Varlamov AV, Voskressensky LG. A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes. Org Lett. 2020 Jun 19;22(12):4726-4731. doi: 10.1021/acs.orglett.0c01530. Epub 2020 Jun 02. PMID: 32484359.
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Modified guanidines as potential chiral superbases. 3. Preparation Of 1,4,6-triazabicyclooctene systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium chloride-induced cyclization of guanidines with a hydroxyethyl substituent.

The Journal of organic chemistry

Isobe T, Fukuda K, Yamaguchi K, Seki H, Tokunaga T, Ishikawa T.
PMID: 11073581
J Org Chem. 2000 Nov 17;65(23):7779-85. doi: 10.1021/jo000746f.

Simple preparation methods of modified guanidines have been explored as potential chiral superbases. Thus, 3,7,8-trisubstituted and 3,6,7, 8-tetrasubstituted 1,4,6-triazabicyclooctene systems were prepared from (1S,2S)-1,2-diphenylethylenediamine through stepwise 2-chloro-1, 3-dimethylimidazolinium chloride (DMC)-induced cyclizations of protected thioureas to the corresponding 2-iminoimidazolidines and...

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Isobe T, Fukuda K, Yamaguchi K, et al. Modified guanidines as potential chiral superbases. 3. Preparation Of 1,4,6-triazabicyclooctene systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium chloride-induced cyclization of guanidines with a hydroxyethyl substituent. J Org Chem. 2000;65(23):7779-85doi: 10.1021/jo000746f.
Isobe, T., Fukuda, K., Yamaguchi, K., Seki, H., Tokunaga, T., & Ishikawa, T. (2000). Modified guanidines as potential chiral superbases. 3. Preparation Of 1,4,6-triazabicyclooctene systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium chloride-induced cyclization of guanidines with a hydroxyethyl substituent. The Journal of organic chemistry, 65(23), 7779-85. https://doi.org/10.1021/jo000746f
Isobe, et al. "Modified guanidines as potential chiral superbases. 3. Preparation Of 1,4,6-triazabicyclooctene systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium chloride-induced cyclization of guanidines with a hydroxyethyl substituent." The Journal of organic chemistry vol. 65,23 (2000): 7779-85. doi: https://doi.org/10.1021/jo000746f
Isobe T, Fukuda K, Yamaguchi K, Seki H, Tokunaga T, Ishikawa T. Modified guanidines as potential chiral superbases. 3. Preparation Of 1,4,6-triazabicyclooctene systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium chloride-induced cyclization of guanidines with a hydroxyethyl substituent. J Org Chem. 2000 Nov 17;65(23):7779-85. doi: 10.1021/jo000746f. PMID: 11073581.
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Nitronyl and imino nitroxides: improvement of Ullman's procedure and report on a new efficient synthetic route.

Chemistry (Weinheim an der Bergstrasse, Germany)

Hirel C, Vostrikova KE, Pécaut J, Ovcharenko VI, Rey P.
PMID: 11405480
Chemistry. 2001 May 04;7(9):2007-14. doi: 10.1002/1521-3765(20010504)7:9<2007::aid-chem2007>3.0.co;2-7.

The synthesis of nitronyl and imino nitroxides has been reexamined with the aim of both increasing yields and of offering opportunities for new structures. The conditions for the formation of 2,3-bis(hydroxyamino)-2,3-dimethylbutane, the key intermediate of Ullman's route, have been...

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Hirel C, Vostrikova KE, Pécaut J, et al. Nitronyl and imino nitroxides: improvement of Ullman's procedure and report on a new efficient synthetic route. Chemistry. 2001;7(9):2007-14doi: 10.1002/1521-3765(20010504)7:9<2007::aid-chem2007>3.0.co;2-7.
Hirel, C., Vostrikova, K. E., Pécaut, J., Ovcharenko, V. I., & Rey, P. (2001). Nitronyl and imino nitroxides: improvement of Ullman's procedure and report on a new efficient synthetic route. Chemistry (Weinheim an der Bergstrasse, Germany), 7(9), 2007-14. https://doi.org/10.1002/1521-3765(20010504)7:9<2007::aid-chem2007>3.0.co;2-7
Hirel, C, et al. "Nitronyl and imino nitroxides: improvement of Ullman's procedure and report on a new efficient synthetic route." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 7,9 (2001): 2007-14. doi: https://doi.org/10.1002/1521-3765(20010504)7:9<2007::aid-chem2007>3.0.co;2-7
Hirel C, Vostrikova KE, Pécaut J, Ovcharenko VI, Rey P. Nitronyl and imino nitroxides: improvement of Ullman's procedure and report on a new efficient synthetic route. Chemistry. 2001 May 04;7(9):2007-14. doi: 10.1002/1521-3765(20010504)7:9<2007::aid-chem2007>3.0.co;2-7. PMID: 11405480.
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Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution.

Organic letters

Coldham I, Copley RC, Haxell TF, Howard S.
PMID: 11700142
Org Lett. 2001 Nov 15;3(23):3799-801. doi: 10.1021/ol016818m.

[reaction--see text] The imidazolidine (tetrahydroimidazole) 2, prepared in one step from N-iso-propylethylenediamine, was subjected to asymmetric lithiation and substitution using sec-butyllithium, (-)-sparteine and a range of electrophiles. Substituted imidazolidines were formed with high optical purity and could be hydrolyzed...

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Coldham I, Copley RC, Haxell TF, et al. Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution. Org Lett. 2001;3(23):3799-801doi: 10.1021/ol016818m.
Coldham, I., Copley, R. C., Haxell, T. F., & Howard, S. (2001). Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution. Organic letters, 3(23), 3799-801. https://doi.org/10.1021/ol016818m
Coldham, I, et al. "Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution." Organic letters vol. 3,23 (2001): 3799-801. doi: https://doi.org/10.1021/ol016818m
Coldham I, Copley RC, Haxell TF, Howard S. Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution. Org Lett. 2001 Nov 15;3(23):3799-801. doi: 10.1021/ol016818m. PMID: 11700142.
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Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction.

Chemical communications (Cambridge, England)

Mukhopadhyay S, Pan SC.
PMID: 29319067
Chem Commun (Camb). 2018 Jan 23;54(8):964-967. doi: 10.1039/c7cc08338f.

The first highly diastereo- and enantioselective synthesis of 2,4-disubstituted imidazolidines has been developed via a formal [3+2] cyclization reaction. Bidentate aminomethyl enones and N-tosyl imines were used as the reaction partners in the reaction. Bifunctional squaramide catalysts were found...

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Mukhopadhyay S, Pan SC. Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction. Chem Commun (Camb). 2018;54(8):964-967doi: 10.1039/c7cc08338f.
Mukhopadhyay, S., & Pan, S. C. (2018). Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction. Chemical communications (Cambridge, England), 54(8), 964-967. https://doi.org/10.1039/c7cc08338f
Mukhopadhyay, Soumendranath, and Pan, Subhas Chandra. "Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction." Chemical communications (Cambridge, England) vol. 54,8 (2018): 964-967. doi: https://doi.org/10.1039/c7cc08338f
Mukhopadhyay S, Pan SC. Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction. Chem Commun (Camb). 2018 Jan 23;54(8):964-967. doi: 10.1039/c7cc08338f. PMID: 29319067.
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Tandem [3 + 2] Cycloaddition/1,4-Addition Reaction of Azomethine Ylides and Aza-o-quinone Methides for Asymmetric Synthesis of Imidazolidines.

Organic letters

Jia H, Liu H, Guo Z, Huang J, Guo H.
PMID: 28898090
Org Lett. 2017 Oct 06;19(19):5236-5239. doi: 10.1021/acs.orglett.7b02512. Epub 2017 Sep 12.

An enantioselective synthesis of biologically important imidazolidines has been achieved via a tandem [3 + 2] cycloaddition/1,4-addition reaction of azomethine ylide and aza-o-quinone methides. With the use of this tool, various imidazolidine derivatives are obtained in good yields with...

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Jia H, Liu H, Guo Z, et al. Tandem [3 + 2] Cycloaddition/1,4-Addition Reaction of Azomethine Ylides and Aza-o-quinone Methides for Asymmetric Synthesis of Imidazolidines. Org Lett. 2017;19(19):5236-5239doi: 10.1021/acs.orglett.7b02512.
Jia, H., Liu, H., Guo, Z., Huang, J., & Guo, H. (2017). Tandem [3 + 2] Cycloaddition/1,4-Addition Reaction of Azomethine Ylides and Aza-o-quinone Methides for Asymmetric Synthesis of Imidazolidines. Organic letters, 19(19), 5236-5239. https://doi.org/10.1021/acs.orglett.7b02512
Jia, Hao, et al. "Tandem [3 + 2] Cycloaddition/1,4-Addition Reaction of Azomethine Ylides and Aza-o-quinone Methides for Asymmetric Synthesis of Imidazolidines." Organic letters vol. 19,19 (2017): 5236-5239. doi: https://doi.org/10.1021/acs.orglett.7b02512
Jia H, Liu H, Guo Z, Huang J, Guo H. Tandem [3 + 2] Cycloaddition/1,4-Addition Reaction of Azomethine Ylides and Aza-o-quinone Methides for Asymmetric Synthesis of Imidazolidines. Org Lett. 2017 Oct 06;19(19):5236-5239. doi: 10.1021/acs.orglett.7b02512. Epub 2017 Sep 12. PMID: 28898090.
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Direct assembly of aldehydes, amino esters, and anilines into chiral imidazolidines via Brønsted acid catalyzed asymmetric 1,3-dipolar cycloadditions.

Organic letters

Liu WJ, Chen XH, Gong LZ.
PMID: 19006395
Org Lett. 2008 Dec 04;10(23):5357-60. doi: 10.1021/ol802177s.

A chiral Brønsted acid catalyzed 1,3-dipolar cycloaddition reaction directly assembles aldehydes, amino esters, and anilines into synthetically useful chiral imidazolidines with high levels of stereoselectivity (up to 91/9 dr and 98% ee).

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Liu WJ, Chen XH, Gong LZ. Direct assembly of aldehydes, amino esters, and anilines into chiral imidazolidines via Brønsted acid catalyzed asymmetric 1,3-dipolar cycloadditions. Org Lett. 2008;10(23):5357-60doi: 10.1021/ol802177s.
Liu, W. J., Chen, X. H., & Gong, L. Z. (2008). Direct assembly of aldehydes, amino esters, and anilines into chiral imidazolidines via Brønsted acid catalyzed asymmetric 1,3-dipolar cycloadditions. Organic letters, 10(23), 5357-60. https://doi.org/10.1021/ol802177s
Liu, Wei-Jun, et al. "Direct assembly of aldehydes, amino esters, and anilines into chiral imidazolidines via Brønsted acid catalyzed asymmetric 1,3-dipolar cycloadditions." Organic letters vol. 10,23 (2008): 5357-60. doi: https://doi.org/10.1021/ol802177s
Liu WJ, Chen XH, Gong LZ. Direct assembly of aldehydes, amino esters, and anilines into chiral imidazolidines via Brønsted acid catalyzed asymmetric 1,3-dipolar cycloadditions. Org Lett. 2008 Dec 04;10(23):5357-60. doi: 10.1021/ol802177s. PMID: 19006395.
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Group 2 Catalysis for the Atom-Efficient Synthesis of Imidazolidine and Thiazolidine Derivatives.

Chemistry (Weinheim an der Bergstrasse, Germany)

Arrowsmith M, Hill MS, Kociok-Köhn G.
PMID: 26094593
Chemistry. 2015 Jul 13;21(29):10548-57. doi: 10.1002/chem.201501328. Epub 2015 Jun 11.

A wide variety of functionalised imidazolidine-2-ones and -thiones, 2-imino-imidazolidines and thiazolidine-2-thiones have been synthesised under very mild reaction conditions by using simple and cost-effective alkaline earth bis(amide) precatalysts, [Ae{N(SiMe3 )2 }2 (THF)2 ] (Ae=Mg, Ca, Sr). The reactions ensue...

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Arrowsmith M, Hill MS, Kociok-Köhn G. Group 2 Catalysis for the Atom-Efficient Synthesis of Imidazolidine and Thiazolidine Derivatives. Chemistry. 2015;21(29):10548-57doi: 10.1002/chem.201501328.
Arrowsmith, M., Hill, M. S., & Kociok-Köhn, G. (2015). Group 2 Catalysis for the Atom-Efficient Synthesis of Imidazolidine and Thiazolidine Derivatives. Chemistry (Weinheim an der Bergstrasse, Germany), 21(29), 10548-57. https://doi.org/10.1002/chem.201501328
Arrowsmith, Merle, et al. "Group 2 Catalysis for the Atom-Efficient Synthesis of Imidazolidine and Thiazolidine Derivatives." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,29 (2015): 10548-57. doi: https://doi.org/10.1002/chem.201501328
Arrowsmith M, Hill MS, Kociok-Köhn G. Group 2 Catalysis for the Atom-Efficient Synthesis of Imidazolidine and Thiazolidine Derivatives. Chemistry. 2015 Jul 13;21(29):10548-57. doi: 10.1002/chem.201501328. Epub 2015 Jun 11. PMID: 26094593.
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Showing 1 to 12 of 28 entries