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 title Project leader Project code Project type Chiral building blocks for biological active molecules. Synthesis and reactivity (Kiralni građevni blokovi za biološki aktivne molekule. Sinteza i reaktivnost)- Zdenko Hameršak 098-0982933-2908 MZOS
Depositing User:	Zdenko Hameršak
Date Deposited:	20 Apr 2016 10:24
URI:	http://fulir.irb.hr/id/eprint/2738
DOI:	10.5562/cca2614

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