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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 (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). pp. 235-240. ISSN 0011-1643

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: cyclic anhydrides; stereoselective alcoholysis; quinine; kinetic resolution; parallel kinetic resolution
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Chiral building blocks for biological active molecules. Synthesis and reactivity (Kiralni građevni blokovi za biološki aktivne molekule. Sinteza i reaktivnost)-Zdenko Hameršak098-0982933-2908MZOS
Depositing User: Zdenko Hameršak
Date Deposited: 20 Apr 2016 10:24
Last Modified: 20 Apr 2016 10:24
URI: http://fulir.irb.hr/id/eprint/2738
DOI: 10.5562/cca2614

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