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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


Puni tekst: engleski pdf 591 Kb

str. 235-240

preuzimanja: 1.129

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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

Posjeta: 1.729 *