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Pregled bibliografske jedinice broj: 121255

Trans Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configuration.


Solladié-Cavallo, A; Roje, Marin; Giraud-Roux, M.; Chen, Y.; Berova, N.; Šunjic, Vitomir
Trans Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configuration. // Chirality, 16 (2004), -; 196-203 (međunarodna recenzija, članak, znanstveni)


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Naslov
Trans Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configuration.

Autori
Solladié-Cavallo, A ; Roje, Marin ; Giraud-Roux, M. ; Chen, Y. ; Berova, N. ; Šunjic, Vitomir

Izvornik
Chirality (0899-0042) 16 (2004); 196-203

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

Ključne riječi
Epoxides; Aryl alcohols; Tweezer cd exciton; Configurations

Sažetak
Anthryl-phenyl, phenanthryl-phenyl, and naphthyl-phenyl trans-epoxides (1, 2, and 3, respectively) having enantiomeric purities of 95%, 99%, and 96% were synthesized from a diastereo and enantiopure sulfonium salt derived from Eliel's oxathiane. The determination of their (1R, 2R) absolute configurations was achieved by application of the CD exciton chirality method using a Zn-porphyrin tweezer on the corresponding alcohols obtained after opening of these epoxides with LiAlH4. The Rconfiguration at C2 of these epoxides, (-)-l, (+)-2, and (-)-3, is consistent with our previous results concerning asymmetric synthesis of monoaryl epoxides, cyclopropanes, and aziridines. The (1 S, 2R) -configuration of the cis isomer (when present) was also confirmed. Moreover, the agreement between the negative exciton chirality for conjugates of (S) -configuration predicted by molecular modeling and the observed CD spectra helps to clarify the relative steric size of phenyl and CH2-aryl (phenanthryl or anthryl), which is critical when the tweezer method is applied for absolute configurational assignment (phenyl = medium group ; anthacenyl CH2 and phenanthryl CH2 large group).

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
0098050

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Marin Roje (autor)

Avatar Url Vitomir Šunjić (autor)


Citiraj ovu publikaciju:

Solladié-Cavallo, A; Roje, Marin; Giraud-Roux, M.; Chen, Y.; Berova, N.; Šunjic, Vitomir
Trans Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configuration. // Chirality, 16 (2004), -; 196-203 (međunarodna recenzija, članak, znanstveni)
Solladié-Cavallo, A., Roje, M., Giraud-Roux, M., Chen, Y., Berova, N. & Šunjic, V. (2004) Trans Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configuration.. Chirality, 16 (-), 196-203.
@article{article, author = {Solladi\'{e}-Cavallo, A and Roje, Marin and Giraud-Roux, M. and Chen, Y. and Berova, N. and \v{S}unjic, Vitomir}, year = {2004}, pages = {196-203}, keywords = {Epoxides, Aryl alcohols, Tweezer cd exciton, Configurations}, journal = {Chirality}, volume = {16}, number = {-}, issn = {0899-0042}, title = {Trans Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configuration.}, keyword = {Epoxides, Aryl alcohols, Tweezer cd exciton, Configurations} }
@article{article, author = {Solladi\'{e}-Cavallo, A and Roje, Marin and Giraud-Roux, M. and Chen, Y. and Berova, N. and \v{S}unjic, Vitomir}, year = {2004}, pages = {196-203}, keywords = {Epoxides, Aryl alcohols, Tweezer cd exciton, Configurations}, journal = {Chirality}, volume = {16}, number = {-}, issn = {0899-0042}, title = {Trans Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configuration.}, keyword = {Epoxides, Aryl alcohols, Tweezer cd exciton, Configurations} }

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
  • MEDLINE


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