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

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Title:Preparation of optically pure enatiomers of Corey lactone by resolution of the racemate
Creators:
Žák, Bohumil
Veselý, Ivan
Neumitka, Karel
Paleček, Jaroslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 8, pp. 1690-1700

Abstract

Racemic hydrogen butanedioates (<i>IIa, IIb</i>) and hydrogen pentanedioates (<i>IIIa, IIIb</i>), prepared by reaction of racemic Corey alcohols <i>Ia, Ib</i> with the corresponding acid anhydride, were resolved by optically active bases [(1<i>R</i>,2<i>S</i>)-(-)-ephedrine, (<i>S</i>)-(-)-1-phenylethylemine, quinine] to give the optically pure diastereoisomeric salts from which the individual enantiomers of hydrogen butanedioate <i>IIa</i> and <i>IIb</i> and hydrogen pentanedioate <i>IIIa</i> and <i>IIIb</i> were liberated. Acid-catalyzed transesterification with methanol converted these optically pure enantiomers into pure(-)-enantiomer <i>Ia</i> and (+)-enantiomer <i>Ib</i> of the Corey lactone.

Title:Preparation of optically pure enatiomers of Corey lactone by resolution of the racemate
Creators:
Žák, Bohumil
Veselý, Ivan
Neumitka, Karel
Paleček, Jaroslav
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:8
Page Range:pp. 1690-1700
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911690UNSPECIFIED
ID Code:5095
Item Type:Article
Deposited On:22 Feb 2010 11:30
Last Modified:22 Feb 2010 10:30

Citation

Žák, Bohumil; Veselý, Ivan; Neumitka, Karel; Paleček, Jaroslav (1991) Preparation of optically pure enatiomers of Corey lactone by resolution of the racemate. Collection of Czechoslovak Chemical Communications, 56 (8). pp. 1690-1700. ISSN 0010-0765

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