Preparation of optically pure enatiomers of Corey lactone by resolution of the racemate

Autor:	Jaroslav Paleček, Karel Neumitka, Ivan Veselý, Bohumil Žák
Rok vydání:	1991
Předmět:	chemistry.chemical_classification Bicyclic molecule Hydrogen chemistry.chemical_element General Chemistry Transesterification Medicinal chemistry Acid anhydride chemistry.chemical_compound chemistry Methanol Enantiomer Enantiomeric excess Lactone
Zdroj:	Collection of Czechoslovak Chemical Communications. 56:1690-1700
ISSN:	1212-6950 0010-0765
DOI:	10.1135/cccc19911690
Popis:	Racemic hydrogen butanedioates (IIa, IIb) and hydrogen pentanedioates (IIIa, IIIb), prepared by reaction of racemic Corey alcohols Ia, Ib with the corresponding acid anhydride, were resolved by optically active bases [(1R,2S)-(-)-ephedrine, (S)-(-)-1-phenylethylemine, quinine] to give the optically pure diastereoisomeric salts from which the individual enantiomers of hydrogen butanedioate IIa and IIb and hydrogen pentanedioate IIIa and IIIb were liberated. Acid-catalyzed transesterification with methanol converted these optically pure enantiomers into pure(-)-enantiomer Ia and (+)-enantiomer Ib of the Corey lactone.
Databáze:	OpenAIRE
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