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Synthesis and alcoholysis of a-alkylated cyclopentane and cyclohexane fused succinic racemic anhydrides in the presence of chiral bases


Lerman, Lidija; Hameršak, Zdenko
Synthesis and alcoholysis of a-alkylated cyclopentane and cyclohexane fused succinic racemic anhydrides in the presence of chiral bases // Croatica Chemica Acta, 88 (2015), 3; 235-240 doi:10.5562/cca2614 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis and alcoholysis of a-alkylated cyclopentane and cyclohexane fused succinic racemic anhydrides in the presence of chiral bases

Autori
Lerman, Lidija ; Hameršak, Zdenko

Izvornik
Croatica Chemica Acta (0011-1643) 88 (2015), 3; 235-240

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

Ključne riječi
cyclic anhydrides; stereoselective alcoholysis; quinine; kinetic resolution; parallel kinetic resolution

Sažetak
Bicyclic succinic anhydrides alkylated at the a-position have been prepared and submitted to alcoholysis in the presence of alkaloid bases. Anhydrides with a cyclopentane fused ring, open only from the less hindered side, generating monoesters of >80% ee, whereas cyclohexane fused anhydrides undergo parallel kinetic resolution, producing both regioisomeric monoesters.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2908 - Kiralni građevni blokovi za biološki aktivne molekule. Sinteza i reaktivnost (Zdenko Hameršak, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Zdenko Hameršak (autor)

Citiraj ovu publikaciju

Lerman, Lidija; Hameršak, Zdenko
Synthesis and alcoholysis of a-alkylated cyclopentane and cyclohexane fused succinic racemic anhydrides in the presence of chiral bases // Croatica Chemica Acta, 88 (2015), 3; 235-240 doi:10.5562/cca2614 (međunarodna recenzija, članak, znanstveni)
Lerman, L. & Hameršak, Z. (2015) Synthesis and alcoholysis of a-alkylated cyclopentane and cyclohexane fused succinic racemic anhydrides in the presence of chiral bases. Croatica Chemica Acta, 88 (3), 235-240 doi:10.5562/cca2614.
@article{article, year = {2015}, pages = {235-240}, DOI = {10.5562/cca2614}, keywords = {cyclic anhydrides, stereoselective alcoholysis, quinine, kinetic resolution, parallel kinetic resolution}, journal = {Croatica Chemica Acta}, doi = {10.5562/cca2614}, volume = {88}, number = {3}, issn = {0011-1643}, title = {Synthesis and alcoholysis of a-alkylated cyclopentane and cyclohexane fused succinic racemic anhydrides in the presence of chiral bases}, keyword = {cyclic anhydrides, stereoselective alcoholysis, quinine, kinetic resolution, parallel kinetic resolution} }

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


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