| dc.creator | Rosso G.B. | |
| dc.date | 2006 | |
| dc.date | 2015-06-30T18:14:05Z | |
| dc.date | 2015-11-26T14:27:53Z | |
| dc.date | 2015-06-30T18:14:05Z | |
| dc.date | 2015-11-26T14:27:53Z | |
| dc.date.accessioned | 2018-03-28T21:31:01Z | |
| dc.date.available | 2018-03-28T21:31:01Z | |
| dc.identifier | | |
| dc.identifier | Synlett. , v. , n. 5, p. 809 - 810, 2006. | |
| dc.identifier | 9365214 | |
| dc.identifier | 10.1055/s-2006-933118 | |
| dc.identifier | http://www.scopus.com/inward/record.url?eid=2-s2.0-33645409850&partnerID=40&md5=febd6fe1d136be66a78f4fb5b1841d0e | |
| dc.identifier | http://www.repositorio.unicamp.br/handle/REPOSIP/103614 | |
| dc.identifier | http://repositorio.unicamp.br/jspui/handle/REPOSIP/103614 | |
| dc.identifier | 2-s2.0-33645409850 | |
| dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1246450 | |
| dc.description | (A) α-Methylation of γ-lactams and γ-lactones: The Bredereck reagent has been employed in the preparation of 4-methylglutamic acids, non-proteinogenic amino acids and analogues with high optical purity and total diastereoselectivity 3,5-cis after hydrogenolysis of enamino lactam intermediate. (B) α-Methylenation of γ-lactams: After preparing the corresponding β-enamino carboxylic system by reaction of a pyroglutamic acid derivative with Bredereck's reagent, its reduction with DIBAL-H afforded the corresponding α-methylene γ-butyro-lactam. (C) α-Amination: Bredereck's reagent has been used as an intermediate for the nitrosation of active methylene groups, followed by reduction of the resulting oxime to afford α-amino lactones and lactams. (D) Introduction of a ketone group α to the carbonyl group: Bredereck's reagent has been employed in the preparation of β-enamino ketones, lactones, esters, substituted amides, or lactams, which after treatment with singlet oxygen using a sensitizer (BANT - bisacenaphthalenethiophene) afford the corresponding α-keto derivatives. (E) Ring-opening polymerization: Recently, Waymouth, Hedrick and co-workers have described the use of Bredereck's reagent as an organic catalyst for the ring-opening polymerization of strained cyclic esters for the synthesis of polylactides. (F) Solid-phase synthesis: The usefulness of the Bredereck's reagent was extended to the solid-phase synthesis of a library of pyrazoles, employing a germanium-based linker, via the formation of enaminones from aromatic ketones. (G) Enamine formation from active methylene compounds: 5-Acyl-6-methyl-2-pyridinones were converted to the corresponding enamines upon treatment with Bredereck's reagent. 1,6-Naphthyridones were obtained in good yields upon treatment of the enamines with ammonium acetate. (H) Indole synthesis: Indoles can be obtained from tetrahydronaphthalenes and Bredereck's reagent via enamine formation assisted by the nitro group in the benzene ring under mild conditions. © Georg Thieme Verlag Stuttgart. | |
| dc.description | | |
| dc.description | 5 | |
| dc.description | 809 | |
| dc.description | 810 | |
| dc.description | Bredereck, H., Simchen, G., Rebsdat, S., Kantlehner, W., Horn, P., Wahl, R., Hoffmann, H., Grieshaber, P., (1968) Chem. Ber., 101, p. 41 | |
| dc.description | Kantlehner, W., Speh, P., (1972) Chem. Ber., 105, p. 1340 | |
| dc.description | Blank, H.U., Kraus, H., Marzolph, G., Müller, N., Patent EP 525536A2, 1993(1993) Chem. Abstr., 118, p. 212507 | |
| dc.description | Coudert, E., Acher, F., Azerad, R., (1997) Synthesis, p. 863 | |
| dc.description | August, R.A., Khan, J.A., Moody, C.M., Young, D.W., (1992) Tetrahedron Lett., 33, p. 4617 | |
| dc.description | August, R.A., Khan, J.A., Moody, C.M., Young, D.W.J., (1996) Chem. Soc., Perkin Trans, 1, p. 507 | |
| dc.description | Skof, M., Svete, J., Kmetic, M., Golic-Grdadolnik, S., Stanovick, B., (1999) Eur. J. Org. Chem., 64, p. 1581 | |
| dc.description | Wasserman, H.H., Ives, J.L., (1985) J. Org. Chem., 50, p. 3573. , and references cited therein | |
| dc.description | Csihony, S., Beaudette, T.T., Sentam, A.C., Nyce, G.W., Waymouth, R.M., Hedrick, J.L., (2004) Adv. Synth. Catal., 346, p. 1081 | |
| dc.description | Spivey, A.C., Diaper, C.M., Adams, H., Rudge, A.J., (2000) J. Org. Chem., 65, p. 5253 | |
| dc.description | Singh, B., Lesher, G., (1990) J. Heterocycl. Chem., 27, p. 2085 | |
| dc.description | Singh, B., Lesher, G., Brundage, R.P., (1991) Synthesis, p. 894 | |
| dc.description | Haefliger, W., Knecht, H., (1983) Tetrahedron Lett., 25, p. 285 | |
| dc.language | en | |
| dc.publisher | | |
| dc.relation | Synlett | |
| dc.rights | aberto | |
| dc.source | Scopus | |
| dc.title | Tert-butoxy Bis(dimethyl-amino)methane (bredereck's Reagent) | |
| dc.type | Artículos de revistas | |
