Izvorni znanstveni članak

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

Sažetak

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.

Ključne riječi

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

Hrčak ID:

150527

URI

https://hrcak.srce.hr/150527

Datum izdavanja:

30.12.2015.

Posjeta: 2.518 *