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Pregled bibliografske jedinice broj: 71320

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


Majerić-Elenkov, Maja; Žiher, Dinko; Višnjevac, Aleksandar; Hameršak, Zdenko; Kojic-Prodic, Biserka; Šunjic, Vitomir
Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers // Croatica Chemica Acta, 74 (2001), 3; 707-724 (međunarodna recenzija, članak, znanstveni)


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

Autori
Majerić-Elenkov, Maja ; Žiher, Dinko ; Višnjevac, Aleksandar ; Hameršak, Zdenko ; Kojic-Prodic, Biserka ; Šunjic, Vitomir

Izvornik
Croatica Chemica Acta (0011-1643) 74 (2001), 3; 707-724

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
1;4-benzodiazepines; Enantioseparation; Hplc chiral chromatography; Relative and absolute configuration

Sažetak
Aldol reaction of C(3) carbanion of 7-bromo-5-pyrido-1,4-benzodiazepin-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˘-phenylmethyl)-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˘-methylethyl)-1-methyl-5-(2'-pyridyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (6/7) with 60-85% diastereoselectivity. For prevailing diastereomeric racemates (ą)-2 and (ą)-4 syn relative configuration is deduced, whereas prevailing diastereomer (ą)-7 has anti configuration. Configurational assignment is based on 1H-NMR data and X-ray structure analysis, and the origin of inversion of diastereoselectivity is discussed. Racemic mixtures are separated on chiral HPLC column, and on the bases of the CD spectra (3R) absolute configuration is determined for (+)-enantiomers, and (3S) 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 diethyl zinc, these ligands proved chemically and configurationally unstable.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
00980608
00980701

Ustanove:
Institut "Ruđer Bošković", Zagreb


Citiraj ovu publikaciju:

Majerić-Elenkov, Maja; Žiher, Dinko; Višnjevac, Aleksandar; Hameršak, Zdenko; Kojic-Prodic, Biserka; Šunjic, Vitomir
Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers // Croatica Chemica Acta, 74 (2001), 3; 707-724 (međunarodna recenzija, članak, znanstveni)
Majerić-Elenkov, M., Žiher, D., Višnjevac, A., Hameršak, Z., Kojic-Prodic, B. & Šunjic, 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.
@article{article, year = {2001}, pages = {707-724}, keywords = {1, 4-benzodiazepines, Enantioseparation, Hplc chiral chromatography, Relative and absolute configuration}, journal = {Croatica Chemica Acta}, volume = {74}, number = {3}, issn = {0011-1643}, title = {Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers}, keyword = {1, 4-benzodiazepines, Enantioseparation, Hplc chiral chromatography, Relative and absolute configuration} }
@article{article, year = {2001}, pages = {707-724}, keywords = {1, 4-benzodiazepines, Enantioseparation, Hplc chiral chromatography, Relative and absolute configuration}, journal = {Croatica Chemica Acta}, volume = {74}, number = {3}, issn = {0011-1643}, title = {Diastereoselective Aldol Reaction of 7-Bromo-5-pyrido-1,4-benzodiazepin-2-one; Relative and Absolute Configuration of All Stereoisomers}, keyword = {1, 4-benzodiazepines, Enantioseparation, Hplc chiral chromatography, Relative and absolute configuration} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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