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Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers

Maja Majerić-Elenkov ; Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, 10002 Zagreb, Croatia
Dinko Žiher ; PLIVA d.d., Research and Development, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia
Aleksandar Višnjevac ; Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, 10002 Zagreb, Croatia
Zdenko Hameršak ; Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, 10002 Zagreb, Croatia
Biserka Kojić-Prodić ; Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, 10002 Zagreb, Croatia
Vitomir Šunjić ; Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, 10002 Zagreb, Croatia

Puni tekst: engleski, pdf (176 KB) str. 707-724 preuzimanja: 152* citiraj
APA 6th Edition
Majerić-Elenkov, M., Žiher, D., Višnjevac, A., Hameršak, Z., Kojić-Prodić, B. i Šunjić, V. (2001). Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers. Croatica Chemica Acta, 74 (3), 707-724. Preuzeto s https://hrcak.srce.hr/131925
MLA 8th Edition
Majerić-Elenkov, Maja, et al. "Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers." Croatica Chemica Acta, vol. 74, br. 3, 2001, str. 707-724. https://hrcak.srce.hr/131925. Citirano 05.03.2021.
Chicago 17th Edition
Majerić-Elenkov, Maja, Dinko Žiher, Aleksandar Višnjevac, Zdenko Hameršak, Biserka Kojić-Prodić i Vitomir Šunjić. "Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers." Croatica Chemica Acta 74, br. 3 (2001): 707-724. https://hrcak.srce.hr/131925
Harvard
Majerić-Elenkov, M., et al. (2001). 'Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers', Croatica Chemica Acta, 74(3), str. 707-724. Preuzeto s: https://hrcak.srce.hr/131925 (Datum pristupa: 05.03.2021.)
Vancouver
Majerić-Elenkov M, Žiher D, Višnjevac A, Hameršak Z, Kojić-Prodić B, Šunjić V. Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers. Croatica Chemica Acta [Internet]. 2001 [pristupljeno 05.03.2021.];74(3):707-724. Dostupno na: https://hrcak.srce.hr/131925
IEEE
M. Majerić-Elenkov, D. Žiher, A. Višnjevac, Z. Hameršak, B. Kojić-Prodić i V. Šunjić, "Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers", Croatica Chemica Acta, vol.74, br. 3, str. 707-724, 2001. [Online]. Dostupno na: https://hrcak.srce.hr/131925. [Citirano: 05.03.2021.]

Sažetak
Aldol reaction of C(3) carbanion of 7-bromo-5-pyrido-1,4-benzodia-zepin-2-one (1) with representative aliphatic and aromatic aldehydes and ketones afforded racemic mixtures syn/anti-7-bromo-3-(1'-hydroxy-1'-phenylmethyl)-1-methyl-5-(2'-pyridyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (2/3), syn/anti-7-bromo-3-(1'-hydroxy-1'-phenylethyl)-1-methyl-5-(2'-pyridyl)-2,3-dihydro-1H-1,4-benzodiazepin -2-one (4/5) and syn/anti-7-bromo-3-(1'-hydroxy-2'-methylpropyl)-1-methyl-5-(2'-pyridyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (6/7) with 60-85% diastereoselectivity. For prevailing diastereomeric racemates (±)-2 and (±)-4, syn relative configuration is deduced, whereas the prevailing diastereomer (±)-7 has anti configuration. Configurational assignment is based on NMR data and X-ray structure analysis, and the origin of inversion of diastereoselectivity is discussed. Racemic mixtures were separated on chiral HPLC column, and on the basis of the CD spectra (3R) absolute configuration was determined for (+)-enantiomers, and (SS) configuration for (-)-enantiomers. Consequently, (3R,1'S) configuration is assigned to syn-(+)-enantiomers and (3R,1'R)-configuration to anti-(+)-enantiomers. In an attempt to use enantiomerically pure compounds 2-7 as catalysts in asymmetric alkylation of benzaldehyde by diethylzinc, these ligands proved chemically and configuration-ally unstable.

Ključne riječi
1,4-benzodiazepines; enantioseparation; HPLC chiral chromatography; relative and absolute configuration

Hrčak ID: 131925

URI
https://hrcak.srce.hr/131925

Posjeta: 269 *