Croatica Chemica Acta, Vol. 88 No. 3, 2015.
Original scientific paper
https://doi.org/10.5562/cca2614
Synthesis and Alcoholysis of α-Alkylated Cyclopentane and Cyclohexane Fused Succinic Racemic Anhydrides in the Presence of Chiral Bases
Lidija Lerman
; PLIVA Research and Development Ltd., Prilaz baruna Filipovića 29, HR-10000 Zagreb, Croatia
Zdenko Hameršak
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Abstract
Bicyclic succinic anhydrides alkylated at the α-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.
Keywords
cyclic anhydrides; stereoselective alcoholysis; quinine; kinetic resolution; parallel kinetic resolution
Hrčak ID:
150527
URI
Publication date:
30.12.2015.
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