Alkyl malolactonates as chiral precursors in the macromolecular engineering of polyesters with a controlled architecture

Racemic and optically active 4-alkyloxycarbonyl-2-oxetanones (alkyl malolactonates) have been prepared starting from malic acid or aspartic acid, and by introducing a chiral alkyl ester group (2-butyl or 3,3-dimethyl-2-butyl) in the course of beta-substituted p-lactones synthesis. Different stereois...

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Bibliographic Details
Published inEnantiomer Vol. 4; no. 5; pp. 379 - 388
Main Authors Bear, MM, Langlois, Veschambre, H, Guerin, P
Format Journal Article
LanguageEnglish
Published READING Taylor & Francis 01.01.1999
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Multidisciplinary
Chemistry, Organic
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
stereoisomers
POLY(BETA-MALIC ACID)
4-ALKYLOXYCARBONYL-2-OXETANONES
MONOMERS
2 STEREOGENIC CENTERS
POLYSTEREOISOMERS
4-(3,3-dimethyl-2-butyl)oxycarbonyl-2-oxetanone
4-(2-butyl)oxycarbonyl-2-oxetanone
DERIVATIVES
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Summary:Racemic and optically active 4-alkyloxycarbonyl-2-oxetanones (alkyl malolactonates) have been prepared starting from malic acid or aspartic acid, and by introducing a chiral alkyl ester group (2-butyl or 3,3-dimethyl-2-butyl) in the course of beta-substituted p-lactones synthesis. Different stereoisomers have been obtained and characterized. It has been shown, by using H-1 NMR and chiral Gas Chromatography, diastereosomeric excess as high as 98% could be retained during the synthesis according to the specific experimental conditions. These new lactones are dedicated to the tailor-making of semi-crystalline and optically active polymeric materials with a well defined configurational structure and fixed thermal properties.
ISSN:1024-2430